RXNO
type: Ontology
version IRI: rxno.owl
description: RXNO is the name reaction ontology. It contains more than 500 classes representing organic reactions such as the Diels–Alder cyclization.
license: http://creativecommons.org/licenses/by/4.0/
date: 16:12:2021 15:55
default-namespace: RXNO
has_obo_format_version: 1.4

definition
type: AnnotationProperty

imported from
type: AnnotationProperty

has_alternative_id
type: AnnotationProperty

has_broad_synonym
type: AnnotationProperty

database_cross_reference
type: AnnotationProperty

has_exact_synonym
type: AnnotationProperty

has_narrow_synonym
type: AnnotationProperty

has_obo_format_version
type: AnnotationProperty

has_obo_namespace
type: AnnotationProperty

has_related_synonym
type: AnnotationProperty

in_subset
type: AnnotationProperty

realizes
type: ObjectProperty
has_obo_namespace: RXNO
id: BFO:0000055

has_participant
type: ObjectProperty
has_obo_namespace: RXNO
id: BFO:0000057

has participant beginning to exist
type: ObjectProperty
sub property of: has_participant
has_obo_namespace: RXNO
id: BFO:0000077

has participant ceasing to exist
type: ObjectProperty
sub property of: has_participant
has_obo_namespace: RXNO
id: BFO:0000078

has disposition at all times
type: ObjectProperty
has_obo_namespace: RXNO
id: BFO:0000162

achieves_planned_objective
type: ObjectProperty
domain: planned process
range: objective specification
definition: This relation obtains between a planned process and a objective specification when the criteria specified in the objective specification are met at the end of the planned process.
has_obo_namespace: RXNO
id: OBI:0000417

Axiom
annotated source: achieves_planned_objective
annotated property: definition
annotated target: This relation obtains between a planned process and a objective specification when the criteria specified in the objective specification are met at the end of the planned process.
database_cross_reference: obi:AR
database_cross_reference: obi:BP
database_cross_reference: obi:PPPBbranch

protects
type: ObjectProperty
sub property of: has participant ceasing to exist
domain: protection reaction
range: group
definition: The notion here is that a given reaction is meant to 'protect' a given group from reacting in a subsequent process and can be 'deprotected' later.
has_obo_namespace: RXNO
id: RXNO:0000416
comment: can we chain 'has specified reactant' (RXNO:0000424) and has_part ?

Axiom
annotated source: protects
annotated property: definition
annotated target: The notion here is that a given reaction is meant to 'protect' a given group from reacting in a subsequent process and can be 'deprotected' later.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

deprotects
type: ObjectProperty
sub property of: has participant beginning to exist
domain: deprotection reaction
range: group
definition: If a reaction R deprotects a group G, then G is in the product where it wasn't in the reactant.
has_obo_namespace: RXNO
id: RXNO:0000417
comment: can we chain 'has specified product' (RXNO:0000423) and has_part ?

Axiom
annotated source: deprotects
annotated property: definition
annotated target: If a reaction R deprotects a group G, then G is in the product where it wasn't in the reactant.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

has specified product
type: ObjectProperty
sub property of: has participant beginning to exist
domain: planned reaction step
range: molecular entity
definition: A relation between a planned reaction step and a molecular entity participating in that process. The creation of the molecular entity during the process is explicitly specified in the objective specification which the planned reaction step realizes the concretization of.
has_obo_namespace: RXNO
id: RXNO:0000423
comment: The difference between this and OBI's has_specified_output is that it is necessary that the participant starts to exist during the process.

Axiom
annotated source: has specified product
annotated property: definition
annotated target: A relation between a planned reaction step and a molecular entity participating in that process. The creation of the molecular entity during the process is explicitly specified in the objective specification which the planned reaction step realizes the concretization of.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

has specified reactant
type: ObjectProperty
sub property of: has participant ceasing to exist
domain: planned reaction step
range: molecular entity
definition: A relation between a planned reaction step and a molecular entity participating in that process that is not created during the process. The destruction of the molecular entity during the process is explicitly specified in the plan specification which the process realizes the concretization of.
has_obo_namespace: RXNO
id: RXNO:0000424
comment: The difference between this and OBI's has_specified_input is that it is necessary that the reactant ceases to exist during the process.

Axiom
annotated source: has specified reactant
annotated property: definition
annotated target: A relation between a planned reaction step and a molecular entity participating in that process that is not created during the process. The destruction of the molecular entity during the process is explicitly specified in the plan specification which the process realizes the concretization of.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

has_catalyst
type: ObjectProperty
sub property of: has_participant
definition: A relation between a planned reaction step and a molecular entity participating in that process that has_role catalyst ((CHEBI:35223).
has_obo_namespace: RXNO
id: RXNO:0000425

Axiom
annotated source: has_catalyst
annotated property: definition
annotated target: A relation between a planned reaction step and a molecular entity participating in that process that has_role catalyst ((CHEBI:35223).
database_cross_reference: https://orcid.org/0000-0001-5985-7429

has_intermediate
type: ObjectProperty
sub property of: has_participant
definition: A relation between a planned reaction step and a molecular entity participating in that process. The creation and subsequent destruction of the molecular entity during the process are explicitly specified in the plan specification which the process realizes the concretization of.
has_obo_namespace: RXNO
id: RXNO:0000469

Axiom
annotated source: has_intermediate
annotated property: definition
annotated target: A relation between a planned reaction step and a molecular entity participating in that process. The creation and subsequent destruction of the molecular entity during the process are explicitly specified in the plan specification which the process realizes the concretization of.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

has_part
type: ObjectProperty
has_obo_namespace: RXNO
id: has_part

part_of
type: ObjectProperty
has_obo_namespace: RXNO
id: part_of

process
type: Class
has_obo_namespace: RXNO
id: BFO:0000015

disposition
type: Class
has_obo_namespace: RXNO
id: BFO:0000016

alkylamine
type: Class
subclass of: primary amine
has_obo_namespace: RXNO
id: CHEBI:13759

alpha-hydroxy ketone
type: Class
subclass of: oxyketone
definition: An alpha-oxyketone that has a hydroxy group as the alpha-oxy moiety.
imported from: http://purl.obolibrary.org/obo/chebi/205/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:139588
in_subset: 3 STAR

dioxygen
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:15379

primary alcohol
type: Class
subclass of: alcohol
has_obo_namespace: RXNO
id: CHEBI:15734

phenol
type: Class
subclass of: phenols
definition: An organic hydroxy compound that consists of benzene bearing a single hydroxy substituent. The parent of the class of phenols.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_alternative_id: CHEBI:14777
has_alternative_id: CHEBI:25966
has_alternative_id: CHEBI:43543
has_alternative_id: CHEBI:8071
has_obo_namespace: chebi_ontology
id: CHEBI:15882
in_subset: 3 STAR

ammonia
type: Class
subclass of: molecular entity
definition: An azane that consists of a single nitrogen atom covelently bonded to three hydrogen atoms.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_alternative_id: CHEBI:13405
has_alternative_id: CHEBI:13406
has_alternative_id: CHEBI:13407
has_alternative_id: CHEBI:13771
has_alternative_id: CHEBI:22533
has_alternative_id: CHEBI:44269
has_alternative_id: CHEBI:44284
has_alternative_id: CHEBI:44404
has_alternative_id: CHEBI:7434
has_obo_namespace: chebi_ontology
id: CHEBI:16134
in_subset: 3 STAR

pyridine
type: Class
subclass of: pyridines
has_obo_namespace: RXNO
id: CHEBI:16227

hydrogen peroxide
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:16240

organic sulfide
type: Class
subclass of: molecular entity
definition: Compounds having the structure RSR (R =/= H). Such compounds were once called thioethers.
has_alternative_id: CHEBI:13694
has_alternative_id: CHEBI:26960
has_alternative_id: CHEBI:9340
has_obo_namespace: chebi_ontology
id: CHEBI:16385
in_subset: 3 STAR

carbon dioxide
type: Class
subclass of: carbon oxide
has_obo_namespace: RXNO
id: CHEBI:16526

dialkyl phosphate
type: Class
subclass of: alkyl phosphate
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_alternative_id: CHEBI:14137
has_alternative_id: CHEBI:23664
has_alternative_id: CHEBI:4486
has_obo_namespace: chebi_ontology
id: CHEBI:16648
in_subset: 3 STAR

peptide
type: Class
subclass of: carboxamide
has_obo_namespace: RXNO
id: CHEBI:16670

formaldehyde
type: Class
subclass of: aldehyde
has_obo_namespace: RXNO
id: CHEBI:16842

ketone
type: Class
subclass of: carbonyl compound
has_obo_namespace: RXNO
id: CHEBI:17087

carbon monoxide
type: Class
subclass of: carbon oxide
definition: A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_alternative_id: CHEBI:13281
has_alternative_id: CHEBI:23013
has_alternative_id: CHEBI:3282
has_alternative_id: CHEBI:41526
has_obo_namespace: chebi_ontology
id: CHEBI:17245
in_subset: 3 STAR

phenylsilane
type: Class
subclass of: organosilicon compound
definition: An organosilicon compound that is benzene in which a hydrogen is replaced by a silyl group.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:172874
in_subset: 3 STAR

aldehyde
type: Class
subclass of: carbonyl compound
has_obo_namespace: RXNO
id: CHEBI:17478

organohalogen compound
type: Class
subclass of: halide
definition: A compound containing at least one carbon-halogen bond (where X is a halogen atom).
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_alternative_id: CHEBI:13444
has_alternative_id: CHEBI:36684
has_alternative_id: CHEBI:8767
has_obo_namespace: chebi_ontology
id: CHEBI:17792
in_subset: 3 STAR

hydrogen chloride
type: Class
subclass of: hydrogen halide
has_obo_namespace: RXNO
id: CHEBI:17883

dinitrogen
type: Class
subclass of: molecular entity
definition: An elemental molecule consisting of two trivalently-bonded nitrogen atoms.
charge: 0
formula: N2
inchi: InChI=1S/N2/c1-2
inchikey: IJGRMHOSHXDMSA-UHFFFAOYSA-N
mass: 28.01348
monoisotopicmass: 28.00615
smiles: N#N
has_alternative_id: CHEBI:13388
has_alternative_id: CHEBI:14660
has_alternative_id: CHEBI:25365
has_alternative_id: CHEBI:43128
has_alternative_id: CHEBI:7593
database_cross_reference: CAS:7727-37-9
database_cross_reference: Drug_Central:4251
database_cross_reference: Gmelin:150
database_cross_reference: HMDB:HMDB0001371
database_cross_reference: KEGG:C00697
database_cross_reference: KEGG:D00083
database_cross_reference: MetaCyc:NITROGEN-MOLECULE
database_cross_reference: PDBeChem:HDZ
database_cross_reference: PMID:18334638
database_cross_reference: PMID:22237545
database_cross_reference: Reaxys:15940095
database_cross_reference: Wikipedia:Nitrogen
has_exact_synonym: dinitrogen
has_obo_namespace: chebi_ontology
has_related_synonym: N#N
has_related_synonym: N2
has_related_synonym: Nitrogen
has_related_synonym: molecular nitrogen
id: CHEBI:17997
in_subset: 3 STAR

Axiom
annotated source: dinitrogen
annotated property: database_cross_reference
annotated target: CAS:7727-37-9
source: NIST Chemistry WebBook

Axiom
annotated source: dinitrogen
annotated property: database_cross_reference
annotated target: Drug_Central:4251
source: DrugCentral

Axiom
annotated source: dinitrogen
annotated property: database_cross_reference
annotated target: Gmelin:150
source: Gmelin

Axiom
annotated source: dinitrogen
annotated property: database_cross_reference
annotated target: PMID:18334638
source: Europe PMC

Axiom
annotated source: dinitrogen
annotated property: database_cross_reference
annotated target: PMID:22237545
source: Europe PMC

Axiom
annotated source: dinitrogen
annotated property: database_cross_reference
annotated target: Reaxys:15940095
source: Reaxys

Axiom
annotated source: dinitrogen
annotated property: has_exact_synonym
annotated target: dinitrogen
database_cross_reference: IUPAC
has synonym type: IUPAC NAME

Axiom
annotated source: dinitrogen
annotated property: has_related_synonym
annotated target: N#N
database_cross_reference: ChEBI

Axiom
annotated source: dinitrogen
annotated property: has_related_synonym
annotated target: N2
database_cross_reference: IUPAC

Axiom
annotated source: dinitrogen
annotated property: has_related_synonym
annotated target: N2
database_cross_reference: KEGG_COMPOUND

Axiom
annotated source: dinitrogen
annotated property: has_related_synonym
annotated target: N2
database_cross_reference: UniProt

Axiom
annotated source: dinitrogen
annotated property: has_related_synonym
annotated target: Nitrogen
database_cross_reference: KEGG_COMPOUND

Axiom
annotated source: dinitrogen
annotated property: has_related_synonym
annotated target: molecular nitrogen
database_cross_reference: ChEBI

Axiom
annotated source: dinitrogen
annotated property: database_cross_reference
annotated target: CAS:7727-37-9
source: ChemIDplus

Axiom
annotated source: dinitrogen
annotated property: database_cross_reference
annotated target: CAS:7727-37-9
source: KEGG COMPOUND

hydrogen halide
type: Class
subclass of: molecular entity
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_alternative_id: CHEBI:13368
has_alternative_id: CHEBI:37140
has_alternative_id: CHEBI:5599
has_obo_namespace: chebi_ontology
id: CHEBI:18140
in_subset: 3 STAR

manganese atom
type: Class
subclass of: transition element atom
definition: A manganese group element atom that has formula Mn.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_alternative_id: CHEBI:13382
has_alternative_id: CHEBI:25153
has_alternative_id: CHEBI:6681
has_obo_namespace: chebi_ontology
id: CHEBI:18291
in_subset: 3 STAR

alkane
type: Class
subclass of: molecular entity
definition: An acyclic branched or unbranched hydrocarbon having the general formula CnH2n+2, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms.
charge: 0
formula: CH3R
mass: 15.035
monoisotopicmass: 15.02348
smiles: C[*]
has_alternative_id: CHEBI:13435
has_alternative_id: CHEBI:22317
has_alternative_id: CHEBI:2576
database_cross_reference: KEGG:C01371
has_exact_synonym: Alkane
has_exact_synonym: alkane
has_exact_synonym: alkanes
has_obo_namespace: chebi_ontology
has_related_synonym: Alkan
has_related_synonym: RH
has_related_synonym: alcane
has_related_synonym: alcanes
has_related_synonym: alcano
has_related_synonym: alcanos
has_related_synonym: an alkane
id: CHEBI:18310
in_subset: 3 STAR

Axiom
annotated source: alkane
annotated property: has_exact_synonym
annotated target: Alkane
database_cross_reference: KEGG_COMPOUND

Axiom
annotated source: alkane
annotated property: has_exact_synonym
annotated target: alkane
database_cross_reference: IUPAC
has synonym type: IUPAC NAME

Axiom
annotated source: alkane
annotated property: has_exact_synonym
annotated target: alkanes
database_cross_reference: IUPAC
has synonym type: IUPAC NAME

Axiom
annotated source: alkane
annotated property: has_related_synonym
annotated target: Alkan
database_cross_reference: ChEBI

Axiom
annotated source: alkane
annotated property: has_related_synonym
annotated target: RH
database_cross_reference: KEGG_COMPOUND

Axiom
annotated source: alkane
annotated property: has_related_synonym
annotated target: alcane
database_cross_reference: IUPAC

Axiom
annotated source: alkane
annotated property: has_related_synonym
annotated target: alcanes
database_cross_reference: IUPAC

Axiom
annotated source: alkane
annotated property: has_related_synonym
annotated target: alcano
database_cross_reference: IUPAC

Axiom
annotated source: alkane
annotated property: has_related_synonym
annotated target: alcanos
database_cross_reference: IUPAC

Axiom
annotated source: alkane
annotated property: has_related_synonym
annotated target: an alkane
database_cross_reference: UniProt

nitrile
type: Class
subclass of: cyanides
has_obo_namespace: RXNO
id: CHEBI:18379

acridines
type: Class
subclass of: fused compound
subclass of: organonitrogen heterocyclic compound
has_obo_namespace: RXNO
id: CHEBI:22213

alkyl phosphate
type: Class
subclass of: organic phosphate
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:22324
in_subset: 3 STAR

alkyne
type: Class
subclass of: molecular entity
definition: Acyclic branched or unbranched hydrocarbons having a carbon-carbon triple bond and the general formula CnH2n-2, RC#CR.
has_obo_namespace: chebi_ontology
id: CHEBI:22339
in_subset: 3 STAR

arenecarbaldehyde
type: Class
subclass of: aldehyde
has_obo_namespace: RXNO
id: CHEBI:33855

azide
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:22680

benzaldehydes
type: Class
subclass of: aldehyde
has_obo_namespace: RXNO
id: CHEBI:22698

benzenes
type: Class
subclass of: benzenoid aromatic compound
definition: Any benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:22712
in_subset: 3 STAR

benzimidazoles
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:22715

bromoalkane
type: Class
subclass of: haloalkane
has_obo_namespace: RXNO
id: CHEBI:22929

carbon oxide
type: Class
subclass of: organooxygen compound
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:23014
in_subset: 3 STAR

carbonyl group
type: Class
subclass of: group
charge: 0
formula: CO
mass: 28.01010
monoisotopicmass: 27.99491
smiles: O=C(*)*
has_exact_synonym: carbonyl
has_exact_synonym: carbonyl group
has_obo_namespace: chebi_ontology
has_related_synonym: >C=O
id: CHEBI:23019
in_subset: 3 STAR

Axiom
annotated source: carbonyl group
annotated property: has_exact_synonym
annotated target: carbonyl
database_cross_reference: IUPAC
has synonym type: IUPAC NAME

Axiom
annotated source: carbonyl group
annotated property: has_exact_synonym
annotated target: carbonyl group
database_cross_reference: ChEBI

Axiom
annotated source: carbonyl group
annotated property: has_exact_synonym
annotated target: carbonyl group
database_cross_reference: UniProt

Axiom
annotated source: carbonyl group
annotated property: has_related_synonym
annotated target: >C=O
database_cross_reference: IUPAC

chalcones
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:23086

chloroalkane
type: Class
subclass of: haloalkane
has_obo_namespace: RXNO
id: CHEBI:23128

cinnamic acids
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:23252

molecular entity
type: Class
subclass of: chemical entity
disjoint with: group
has_obo_namespace: RXNO
id: CHEBI:23367

cyanides
type: Class
subclass of: organonitrogen compound
definition: Salts and C-organyl derivatives of hydrogen cyanide, HC#N.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:23424
in_subset: 3 STAR

flavones
type: Class
subclass of: oxacycle
has_obo_namespace: RXNO
id: CHEBI:24043

formamides
type: Class
subclass of: carboximides
has_obo_namespace: RXNO
id: CHEBI:24079

furans
type: Class
subclass of: oxacycle
has_obo_namespace: RXNO
id: CHEBI:24129

chemical entity
type: Class
has_obo_namespace: RXNO
id: CHEBI:24431

group
type: Class
subclass of: chemical entity
has_obo_namespace: RXNO
id: CHEBI:24433

haloalkane
type: Class
subclass of: halohydrocarbon
has_obo_namespace: RXNO
id: CHEBI:24469

halohydrocarbon
type: Class
subclass of: organohalogen compound
definition: A compound derived from a hydrocarbon by replacing a hydrogen atom with a halogen atom.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:24472
in_subset: 3 STAR

indoles
type: Class
subclass of: fused compound
subclass of: organonitrogen heterocyclic compound
has_obo_namespace: RXNO
id: CHEBI:24828

lactone
type: Class
subclass of: oxacycle
has_obo_namespace: RXNO
id: CHEBI:25000

nitrotoluene
type: Class
subclass of: toluenes
definition: Any member of the class of toluenes bearing one or more nitro substituents on the benzene ring.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:25566
in_subset: 3 STAR

ether
type: Class
subclass of: organooxygen compound
has_obo_namespace: RXNO
id: CHEBI:25698

organic phosphate
type: Class
subclass of: organophosphorus compound
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:25703
in_subset: 3 STAR

organometallic compound
type: Class
subclass of: molecular entity
definition: A compound having bonds between one or more metal atoms and one or more carbon atoms of an organyl group.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:25707
in_subset: 3 STAR

organophosphorus compound
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:25710

organosilicon compound
type: Class
subclass of: molecular entity
definition: An organosilicon compound is a compound containing at least one carbon-silicon bond.
has_exact_synonym: organosilicon compound
has_obo_namespace: chebi_ontology
has_related_synonym: organosilicon compounds
has_related_synonym: silicoorganic compounds
id: CHEBI:25713
in_subset: 3 STAR

Axiom
annotated source: organosilicon compound
annotated property: has_exact_synonym
annotated target: organosilicon compound
database_cross_reference: ChEBI

Axiom
annotated source: organosilicon compound
annotated property: has_related_synonym
annotated target: organosilicon compounds
database_cross_reference: ChEBI

Axiom
annotated source: organosilicon compound
annotated property: has_related_synonym
annotated target: silicoorganic compounds
database_cross_reference: ChEBI

organotin compound
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:25717

oxime
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:25750

phenylhydrazine
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:25996

amidine
type: Class
subclass of: molecular entity
definition: Derivatives of oxoacids RnE(=O)OH in which the hydroxy group is replaced by an amino group and the oxo group is replaced by =NR. In organic chemistry an unspecified amidine is commonly a carboxamidine.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:2634
in_subset: 3 STAR

pyrans
type: Class
subclass of: oxacycle
imported from: http://purl.obolibrary.org/obo/chebi/205/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:26407
in_subset: 3 STAR

pyrazoles
type: Class
subclass of: organonitrogen heterocyclic compound
has_obo_namespace: RXNO
id: CHEBI:26410

pyridines
type: Class
subclass of: organonitrogen heterocyclic compound
has_obo_namespace: RXNO
id: CHEBI:26421

pyrroles
type: Class
subclass of: organonitrogen heterocyclic compound
has_obo_namespace: RXNO
id: CHEBI:26455

quinolines
type: Class
subclass of: organonitrogen heterocyclic compound
has_obo_namespace: RXNO
id: CHEBI:26513

radical
type: Class
subclass of: molecular entity
definition: A molecular entity possessing an unpaired electron.
imported from: http://purl.obolibrary.org/obo/chebi/205/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:26519
in_subset: 3 STAR

triazines
type: Class
subclass of: organonitrogen heterocyclic compound
has_obo_namespace: RXNO
id: CHEBI:26588

sodium atom
type: Class
subclass of: metal atom
has_obo_namespace: RXNO
id: CHEBI:26708

tertiary alcohol
type: Class
subclass of: alcohol
has_obo_namespace: RXNO
id: CHEBI:26878

thiophenes
type: Class
subclass of: organosulfur heterocyclic compound
has_obo_namespace: RXNO
id: CHEBI:26961

toluenes
type: Class
subclass of: benzenes
definition: Any member of the class of benzenes that is a substituted benzene in which the substituents include one (and only one) methyl group.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:27024
in_subset: 3 STAR

transition element atom
type: Class
subclass of: metal atom
has_obo_namespace: RXNO
id: CHEBI:27081

zinc atom
type: Class
subclass of: transition element atom
has_obo_namespace: RXNO
id: CHEBI:27363

tetrachloromethane
type: Class
subclass of: chloroalkane
has_obo_namespace: RXNO
id: CHEBI:27385

isatin
type: Class
subclass of: indoles
has_obo_namespace: RXNO
id: CHEBI:27539

sodium azide
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:278547

nickel atom
type: Class
subclass of: transition element atom
has_obo_namespace: RXNO
id: CHEBI:28112

phosphorus atom
type: Class
subclass of: atom
has_obo_namespace: RXNO
id: CHEBI:28659

copper atom
type: Class
subclass of: transition element atom
has_obo_namespace: RXNO
id: CHEBI:28694

flavonols
type: Class
subclass of: oxacycle
has_obo_namespace: RXNO
id: CHEBI:28802

dibromine
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:29224

thiol
type: Class
subclass of: molecular entity
definition: An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.
has_alternative_id: CHEBI:13443
has_alternative_id: CHEBI:13696
has_alternative_id: CHEBI:17366
has_alternative_id: CHEBI:26969
has_alternative_id: CHEBI:8766
has_alternative_id: CHEBI:9556
has_obo_namespace: chebi_ontology
id: CHEBI:29256
in_subset: 3 STAR

sulfanyl
type: Class
subclass of: molecular entity
definition: A sulfur hydride that has formula HS.
has_obo_namespace: chebi_ontology
id: CHEBI:29312
in_subset: 3 STAR

nitro group
type: Class
subclass of: group
has_obo_namespace: RXNO
id: CHEBI:29785

diazene
type: Class
subclass of: molecular entity
charge: 0
formula: H2N2
inchi: InChI=1S/H2N2/c1-2/h1-2H
inchikey: RAABOESOVLLHRU-UHFFFAOYSA-N
mass: 30.02936
monoisotopicmass: 30.02180
smiles: N=N
database_cross_reference: CAS:3618-05-1
database_cross_reference: KEGG:C05360
has_exact_synonym: diazene
has_obo_namespace: chebi_ontology
has_related_synonym: Diimide
has_related_synonym: HN=NH
id: CHEBI:30096
in_subset: 3 STAR

Axiom
annotated source: diazene
annotated property: database_cross_reference
annotated target: CAS:3618-05-1
source: ChemIDplus

Axiom
annotated source: diazene
annotated property: database_cross_reference
annotated target: CAS:3618-05-1
source: NIST Chemistry WebBook

Axiom
annotated source: diazene
annotated property: has_exact_synonym
annotated target: diazene
database_cross_reference: IUPAC
has synonym type: IUPAC NAME

Axiom
annotated source: diazene
annotated property: has_related_synonym
annotated target: Diimide
database_cross_reference: NIST_Chemistry_WebBook

Axiom
annotated source: diazene
annotated property: has_related_synonym
annotated target: HN=NH
database_cross_reference: IUPAC

alcohol
type: Class
subclass of: organic hydroxy compound
has_obo_namespace: RXNO
id: CHEBI:30879

indolin-2-one
type: Class
subclass of: indoles
definition: An indolinone carrying an oxo group at position 2.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:31697
in_subset: 3 STAR

pyruvic acid
type: Class
subclass of: carboxylic acid
subclass of: aromatic amine
has_obo_namespace: RXNO
id: CHEBI:32816

secondary amine
type: Class
subclass of: amine
has_obo_namespace: RXNO
id: CHEBI:32863

tertiary amine
type: Class
subclass of: amine
has_obo_namespace: RXNO
id: CHEBI:32876

primary amine
type: Class
subclass of: amine
has_obo_namespace: RXNO
id: CHEBI:32877

alkene
type: Class
subclass of: olefin
has_obo_namespace: RXNO
id: CHEBI:32878

amine
type: Class
subclass of: organic amino compound
has_obo_namespace: RXNO
id: CHEBI:32952

epoxide
type: Class
subclass of: oxacycle
has_obo_namespace: RXNO
id: CHEBI:32955

amide
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:32988

atom
type: Class
subclass of: chemical entity
has_obo_namespace: RXNO
id: CHEBI:33250

primary amide
type: Class
subclass of: amide
has_obo_namespace: RXNO
id: CHEBI:33256

elemental molecular entity
type: Class
subclass of: molecular entity
definition: A molecular entity all atoms of which have the same atomic number.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:33259
in_subset: 3 STAR

carboxylic ester
type: Class
subclass of: carbonyl compound
has_obo_namespace: RXNO
id: CHEBI:33308

aryl group
type: Class
subclass of: group
has_obo_namespace: RXNO
id: CHEBI:33338

titanium atom
type: Class
subclass of: transition element atom
has_obo_namespace: RXNO
id: CHEBI:33341

palladium atom
type: Class
subclass of: transition element atom
has_obo_namespace: RXNO
id: CHEBI:33363

platinum atom
type: Class
subclass of: transition element atom
has_obo_namespace: RXNO
id: CHEBI:33364

elemental sulfur
type: Class
subclass of: elemental molecular entity
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:33403
in_subset: 3 STAR

elemental halogen
type: Class
subclass of: elemental molecular entity
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:33434
in_subset: 3 STAR

metal atom
type: Class
subclass of: atom
has_obo_namespace: RXNO
id: CHEBI:33521

carboxylic acid
type: Class
subclass of: carbonyl compound
has_obo_namespace: RXNO
id: CHEBI:33575

cyclic compound
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:33595

homocyclic compound
type: Class
subclass of: cyclic compound
definition: A cyclic compound having as ring members atoms of the same element only.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:33597
in_subset: 3 STAR

carbocyclic compound
type: Class
subclass of: homocyclic compound
definition: A homocyclic compound in which all of the ring members are carbon atoms.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:33598
in_subset: 3 STAR

polycyclic compound
type: Class
subclass of: cyclic compound
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:33635
in_subset: 3 STAR

olefin
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:33641

aromatic compound
type: Class
subclass of: cyclic compound
definition: A cyclically conjugated molecular entity with a stability (due to delocalization) significantly greater than that of a hypothetical localized structure (e.g. Kekule structure) is said to possess aromatic character.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:33655
in_subset: 3 STAR

arene
type: Class
subclass of: organic aromatic compound
has_obo_namespace: RXNO
id: CHEBI:33658

organic aromatic compound
type: Class
subclass of: aromatic compound
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:33659
in_subset: 3 STAR

heteropolycyclic compound
type: Class
subclass of: polycyclic compound
definition: A polycyclic compound in which at least one of the rings contains at least one non-carbon atom.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:33671
in_subset: 3 STAR

organic hydroxy compound
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:33822

enol
type: Class
subclass of: organic hydroxy compound
has_obo_namespace: RXNO
id: CHEBI:33823

benzenoid aromatic compound
type: Class
subclass of: organic aromatic compound
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:33836
in_subset: 3 STAR

macromolecule
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:33839

monocyclic arene
type: Class
subclass of: arene
definition: A monocyclic aromatic hydrocarbon.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:33847
in_subset: 3 STAR

polycyclic arene
type: Class
subclass of: arene
definition: A polycyclic aromatic hydrocarbon.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:33848
in_subset: 3 STAR

phenols
type: Class
subclass of: organic aromatic compound
subclass of: organic hydroxy compound
has_obo_namespace: RXNO
id: CHEBI:33853

aromatic amine
type: Class
subclass of: organic aromatic compound
subclass of: organic amino compound
has_obo_namespace: RXNO
id: CHEBI:33860

chloroform
type: Class
subclass of: chloroalkane
has_obo_namespace: RXNO
id: CHEBI:35255

fused compound
type: Class
subclass of: polycyclic compound
has_obo_namespace: RXNO
id: CHEBI:35293

organonitrogen compound
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:35352

isocyanide
type: Class
subclass of: organonitrogen compound
definition: The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:35353
in_subset: 3 STAR

chromium coordination entity
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:35403

1,2,3-triazole
type: Class
subclass of: triazole
has_obo_namespace: RXNO
id: CHEBI:35562

carboximides
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:35636

secondary alcohol
type: Class
subclass of: alcohol
has_obo_namespace: RXNO
id: CHEBI:35681

tetrazoles
type: Class
subclass of: organonitrogen heterocyclic compound
has_obo_namespace: RXNO
id: CHEBI:35689

ester
type: Class
subclass of: organooxygen compound
definition: A compound formally derived from an oxoacid RkE(=O)l(OH)m (l > 0) and an alcohol, phenol, heteroarenol, or enol by linking with formal loss of water from an acidic hydroxy group of the former and a hydroxy group of the latter.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_alternative_id: CHEBI:23960
has_alternative_id: CHEBI:4859
has_obo_namespace: chebi_ontology
id: CHEBI:35701
in_subset: 3 STAR

nitro compound
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:35715

carboxylic anhydride
type: Class
subclass of: acid anhydride
has_obo_namespace: RXNO
id: CHEBI:35873

tertiary phosphine
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:35886

carbonyl compound
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:36587

triphenylphosphane oxide
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:36601

phthalic anhydride
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:36605

acid anhydride
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:36606

acyl chloride
type: Class
subclass of: acyl halide
has_obo_namespace: RXNO
id: CHEBI:36687

pseudohalo group
type: Class
subclass of: group
has_obo_namespace: RXNO
id: CHEBI:36823

inorganic radical
type: Class
subclass of: radical
imported from: http://purl.obolibrary.org/obo/chebi/205/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:36871
in_subset: 3 STAR

organic radical
type: Class
subclass of: radical
imported from: http://purl.obolibrary.org/obo/chebi/205/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:36872
in_subset: 3 STAR

organooxygen compound
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:36963

bromoarene
type: Class
subclass of: haloarene
has_obo_namespace: RXNO
id: CHEBI:37148

halide
type: Class
subclass of: molecular entity
definition: Any heteroatomic molecular entity that is a chemical compound of halogen with other chemical elements.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:37578
in_subset: 3 STAR

acyl halide
type: Class
subclass of: halide
has_obo_namespace: RXNO
id: CHEBI:37579

organic phosphonate
type: Class
subclass of: organophosphorus compound
has_obo_namespace: RXNO
id: CHEBI:37592

allenes
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:37602

cyclohexadiene
type: Class
subclass of: carbocyclic compound
subclass of: olefin
has_obo_namespace: RXNO
id: CHEBI:37613

carboxamide
type: Class
subclass of: primary amide
has_obo_namespace: RXNO
id: CHEBI:37622

phosphonic ester
type: Class
subclass of: ester
definition: A phosphonic acid derivative in which one or both OH groups have been esterified.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_alternative_id: CHEBI:26068
has_alternative_id: CHEBI:4861
has_obo_namespace: chebi_ontology
id: CHEBI:37735
in_subset: 3 STAR

iodoalkane
type: Class
subclass of: haloalkane
has_obo_namespace: RXNO
id: CHEBI:37757

pyranone
type: Class
subclass of: pyrans
definition: Any of a class of cyclic chemical compounds that contain an unsaturated six-membered ring with one ring oxygen atom and an oxo substituent.
imported from: http://purl.obolibrary.org/obo/chebi/205/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:37963
in_subset: 3 STAR

organonitrogen heterocyclic compound
type: Class
subclass of: organonitrogen compound
subclass of: heterocyclic compound
definition: Any organonitrogen compound containing a cyclic component with nitrogen and at least one other element as ring member atoms.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: RXNO
has_obo_namespace: chebi_ontology
id: CHEBI:38101
in_subset: 3 STAR

oxacycle
type: Class
subclass of: heterocyclic compound
has_obo_namespace: RXNO
id: CHEBI:38104

organosulfur heterocyclic compound
type: Class
subclass of: heterocyclic compound
has_exact_synonym: thiacycle
has_obo_namespace: RXNO
id: CHEBI:38106
comment: I think this is the same as a thiacycle but need to check.

organic heteropolycyclic compound
type: Class
subclass of: heteropolycyclic compound
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_alternative_id: CHEBI:25429
has_alternative_id: CHEBI:38075
has_obo_namespace: chebi_ontology
id: CHEBI:38166
in_subset: 3 STAR

boronic acids
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:38269

triazole
type: Class
subclass of: organonitrogen compound
has_obo_namespace: RXNO
id: CHEBI:38597

isoflavones
type: Class
subclass of: oxacycle
has_obo_namespace: RXNO
id: CHEBI:38757

oxetanes
type: Class
subclass of: oxacycle
has_obo_namespace: RXNO
id: CHEBI:38784

alkylbenzene
type: Class
subclass of: benzenes
subclass of: monocyclic arene
definition: A monocyclic arene that is benzene substituted with one or more alkyl groups.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:38976
in_subset: 3 STAR

Brønsted acid
type: Class
subclass of: disposition
has_obo_namespace: RXNO
id: CHEBI:39141

Brønsted base
type: Class
subclass of: disposition
has_obo_namespace: RXNO
id: CHEBI:39142

Lewis acid
type: Class
subclass of: disposition
has_obo_namespace: RXNO
id: CHEBI:39143

Lewis base
type: Class
subclass of: disposition
has_obo_namespace: RXNO
id: CHEBI:39144

halomethane
type: Class
subclass of: haloalkane
definition: A haloalkane that is methane in which one (or more) of the hydrogens have been replaced by a halogen atom/halogen atoms.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:39279
in_subset: 3 STAR

pyrimidines
type: Class
subclass of: organonitrogen heterocyclic compound
has_obo_namespace: RXNO
id: CHEBI:39447

aminoxyls
type: Class
subclass of: organic radical
definition: Radicals derived from hydroxylamines by removal of the hydrogen atom from the hydroxy group. The synonymous terms nitroxyl radicals and nitroxides erroneously suggest the presence of a nitro group.
imported from: http://purl.obolibrary.org/obo/chebi/205/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:39477
in_subset: 3 STAR

formyl group
type: Class
subclass of: group
has_obo_namespace: RXNO
id: CHEBI:42485

hydroxy group
type: Class
subclass of: group
has_obo_namespace: RXNO
id: CHEBI:43176

propane-1,3-dithiol
type: Class
subclass of: thiol
definition: A dithiol that is propane substituted by thiol groups at positions 1 ans 3.
imported from: http://purl.obolibrary.org/obo/chebi/200/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:44864
in_subset: 3 STAR

amino group
type: Class
subclass of: amino groups
has_obo_namespace: RXNO
id: CHEBI:46882

carboxy group
type: Class
subclass of: group
has_obo_namespace: RXNO
id: CHEBI:46883

hydrogen bromide
type: Class
subclass of: hydrogen halide
has_obo_namespace: RXNO
id: CHEBI:47266

tetrabromomethane
type: Class
subclass of: bromoalkane
has_obo_namespace: RXNO
id: CHEBI:47875

enol ether
type: Class
subclass of: ether
definition: Ethers ROR' where R has a double bond adjacent to the oxygen of the ether linkage.
imported from: http://purl.obolibrary.org/obo/chebi/205/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:47985
in_subset: 3 STAR

silyl enol ether
type: Class
subclass of: enol ether
definition: Enol ethers ROR' where R' has the structure SiR''R'''R''''.
imported from: http://purl.obolibrary.org/obo/chebi/205/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:47986
in_subset: 3 STAR

silyl ether
type: Class
subclass of: ether
subclass of: organosilicon compound
definition: Ethers ROR' where R' has the structure SiR''R'''R''''.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:47988
in_subset: 3 STAR

chromium trioxide
type: Class
subclass of: chromium coordination entity
has_obo_namespace: RXNO
id: CHEBI:48420

carbazoles
type: Class
subclass of: fused compound
subclass of: organonitrogen heterocyclic compound
has_obo_namespace: RXNO
id: CHEBI:48513

thiazoles
type: Class
subclass of: organosulfur heterocyclic compound
subclass of: azole
definition: An azole in which the five-membered heterocyclic aromatic skeleton contains a N atom and one S atom.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:48901
in_subset: 3 STAR

copper(II) chloride
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:49553

organic amino compound
type: Class
subclass of: organonitrogen compound
definition: A compound formally derived from ammonia by replacing one, two or three hydrogen atoms by organyl groups.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:50047
in_subset: 3 STAR

dihydropyridine
type: Class
subclass of: organonitrogen heterocyclic compound
has_obo_namespace: RXNO
id: CHEBI:50075

hydroxyaldehyde
type: Class
subclass of: aldehyde
imported from: http://purl.obolibrary.org/obo/chebi/205/chebi.owl
has_alternative_id: CHEBI:24671
has_alternative_id: CHEBI:5798
has_obo_namespace: chebi_ontology
id: CHEBI:50413
in_subset: 3 STAR

pivalate ester
type: Class
subclass of: carboxylic ester
has_obo_namespace: RXNO
id: CHEBI:50784

haloarene
type: Class
subclass of: halohydrocarbon
definition: A compound derived from an arene by replacing a hydrogen atom with a halogen atom.
imported from: http://purl.obolibrary.org/obo/chebi/200/chebi.owl
has_obo_namespace: RXNO
has_obo_namespace: chebi_ontology
id: CHEBI:50887
in_subset: 3 STAR

fluoroarene
type: Class
subclass of: haloarene
has_obo_namespace: RXNO
id: CHEBI:50888

boronate
type: Class
subclass of: molecular entity
definition: A salt or ester of boronic acid.
imported from: http://purl.obolibrary.org/obo/chebi/200/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:50978
in_subset: 3 STAR

nitrate ester
type: Class
subclass of: organooxygen compound
has_obo_namespace: RXNO
id: CHEBI:51080

amino groups
type: Class
subclass of: group
has_obo_namespace: RXNO
id: CHEBI:51142

phosphonium ylide
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:51154

organolithium compound
type: Class
subclass of: organometallic compound
definition: A compound containing at least one carbon-lithium bond.
imported from: http://purl.obolibrary.org/obo/chebi/200/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:51186
in_subset: 3 STAR

organomagnesium compound
type: Class
subclass of: organometallic compound
definition: A compound containing at least one carbon-magnesium bond.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:51187
in_subset: 3 STAR

organomagnesium halide
type: Class
subclass of: organomagnesium compound
has_obo_namespace: RXNO
id: CHEBI:51236

thioester
type: Class
subclass of: carbonyl compound
definition: A compound of general formula RC(=O)SR'. Compare with thionoester, RC(=S)OR'.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:51277
in_subset: 3 STAR

cyclopropanes
type: Class
subclass of: carbocyclic compound
has_obo_namespace: RXNO
id: CHEBI:51454

alkyllithium compound
type: Class
subclass of: organolithium compound
definition: An organolithium compound where an alkyl group is bound to a lithium atom.
imported from: http://purl.obolibrary.org/obo/chebi/200/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:51462
in_subset: 3 STAR

butyllithium
type: Class
subclass of: alkyllithium compound
definition: An alkyllithium compound that has formula C4H9Li.
imported from: http://purl.obolibrary.org/obo/chebi/200/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:51469
in_subset: 3 STAR

organozinc compound
type: Class
subclass of: organometallic compound
definition: A compound containing at least one carbon-zinc bond.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:51494
in_subset: 3 STAR

diarylmethane
type: Class
subclass of: organic aromatic compound
definition: Any compound containing two aryl groups connected by a single C atom.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:51614
in_subset: 3 STAR

alpha,beta-unsaturated ketone
type: Class
subclass of: ketone
has_obo_namespace: RXNO
id: CHEBI:51721

alpha-haloketone
type: Class
subclass of: ketone
subclass of: organohalogen compound
definition: A haloketone in which the halogen and oxo substituents are on adjacent carbon atoms.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:51839
in_subset: 3 STAR

beta-ketoester
type: Class
subclass of: ketone
subclass of: carboxylic ester
has_obo_namespace: RXNO
id: CHEBI:51849

methyl ketone
type: Class
subclass of: ketone
definition: A ketone of formula RC(=O)CH3 (R =/= H).
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:51867
in_subset: 3 STAR

arylacetylene
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:51929

peroxy acid
type: Class
subclass of: carbonyl compound
has_obo_namespace: RXNO
id: CHEBI:52094

oxyketone
type: Class
subclass of: ketone
definition: A compound with the general formula R2C=O (R=/=H) where one or more of the R groups contains an oxy (-O-) group.
imported from: http://purl.obolibrary.org/obo/chebi/205/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:52395
in_subset: 3 STAR

isocyanates
type: Class
subclass of: organonitrogen compound
subclass of: organooxygen compound
has_obo_namespace: RXNO
id: CHEBI:53212

palladium(II) chloride
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:53434

beta-hydroxy ketone
type: Class
subclass of: oxyketone
has_obo_namespace: RXNO
id: CHEBI:55380

hemiacetal
type: Class
subclass of: alcohol
definition: A compound having the general formula RR'C(OH)OR'' (R'' =/= H).
charge: 0
formula: CH2O2R2
mass: 46.025
monoisotopicmass: 46.00548
has_exact_synonym: Hemiacetal
has_exact_synonym: hemiacetals
has_obo_namespace: chebi_ontology
has_related_synonym: hemiacetals
id: CHEBI:5653
in_subset: 3 STAR

Axiom
annotated source: hemiacetal
annotated property: has_exact_synonym
annotated target: Hemiacetal
database_cross_reference: KEGG_COMPOUND

Axiom
annotated source: hemiacetal
annotated property: has_exact_synonym
annotated target: hemiacetals
database_cross_reference: IUPAC
has synonym type: IUPAC NAME

Axiom
annotated source: hemiacetal
annotated property: has_related_synonym
annotated target: hemiacetals
database_cross_reference: ChEBI

heterocyclic compound
type: Class
subclass of: cyclic compound
has_obo_namespace: RXNO
id: CHEBI:5686

phosphine oxide
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:59656

acetal
type: Class
subclass of: organooxygen compound
definition: An organooxygen compound having the structure RR'C(OR'')(OR''') (R'', R''' =/= H). Mixed acetals have R'' and R''' groups which differ.
has_obo_namespace: chebi_ontology
has_related_synonym: acetals
id: CHEBI:59769
in_subset: 3 STAR

Axiom
annotated source: acetal
annotated property: has_related_synonym
annotated target: acetals
database_cross_reference: ChEBI

enyne
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:59831

chemical substance
type: Class
subclass of: chemical entity
definition: A chemical substance is a portion of matter of constant composition, composed of molecular entities of the same type or of different types.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:59999
in_subset: 3 STAR

mixture
type: Class
subclass of: chemical substance
definition: A mixture is a chemical substance composed of multiple molecules, at least two of which are of a different kind.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:60004
in_subset: 3 STAR

polymer
type: Class
subclass of: mixture
definition: A polymer is a mixture, which is composed of macromolecules of different kinds and which may be differentiated by composition, length, degree of branching etc..
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:60027
in_subset: 3 STAR

alkylphosphonate
type: Class
subclass of: organic phosphonate
definition: An organic phosphonate containing a C-PO(OH)2 or C-PO(OR)2 group (where R = alkyl group).
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_alternative_id: CHEBI:2591
has_obo_namespace: chebi_ontology
id: CHEBI:60983
in_subset: 3 STAR

aminophosphonate
type: Class
subclass of: organonitrogen compound
subclass of: organic phosphonate
definition: An organic phosphonate of formula (RO)2P(=O)-CR2-NR2; R can be H.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:61111
in_subset: 3 STAR

azole
type: Class
subclass of: organonitrogen heterocyclic compound
definition: Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.
imported from: http://purl.obolibrary.org/obo/chebi/206/chebi.owl
has_obo_namespace: chebi_ontology
id: CHEBI:68452
in_subset: 3 STAR

organic molecule
type: Class
subclass of: molecular entity
has_obo_namespace: RXNO
id: CHEBI:72695

acetylenic compound
type: Class
subclass of: organic molecule
has_obo_namespace: RXNO
id: CHEBI:73474

terminal acetylenic compound
type: Class
subclass of: acetylenic compound
has_obo_namespace: RXNO
id: CHEBI:73477

objective specification
type: Class
subclass of: information content entity
has_obo_namespace: RXNO
id: IAO:0000005

information content entity
type: Class
has_obo_namespace: RXNO
id: IAO:0000030

formylation
type: Class
subclass of: acylation
subclass of: Restriction
  on property: has_participant
  some values from: formyl group
definition: Formation of a covalent bond between a substrate and a formyl group.
has_exact_synonym: formylation
has_obo_namespace: RXNO
id: MOP:0000003

Axiom
annotated source: formylation
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and a formyl group.
database_cross_reference: RSC:xp

silylation
type: Class
subclass of: formation of covalent bond with group
definition: Formation of a covalent bond between a substrate and an silyl group.
has_exact_synonym: silylation
has_obo_namespace: RXNO
id: MOP:0000339
comment: has_participant: CHEBI:33478

Axiom
annotated source: silylation
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and an silyl group.
database_cross_reference: RSC:xp

methylation
type: Class
subclass of: alkylation
has_obo_namespace: RXNO
id: MOP:0000364

alkylation
type: Class
subclass of: hydrocarbylation
definition: Formation of a covalent bond between a substrate and an alkyl group.
has_exact_synonym: alkylation
has_obo_namespace: RXNO
id: MOP:0000369
comment: has_participant: CHEBI:22323

Axiom
annotated source: alkylation
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and an alkyl group.
database_cross_reference: RSC:xp

hydrocarbylation
type: Class
subclass of: organylation
definition: Formation of a covalent bond between a substrate and a hydrocarbyl group.
has_exact_synonym: hydrocarbylation
has_obo_namespace: RXNO
id: MOP:0000410
comment: has_participant: CHEBI:33248

Axiom
annotated source: hydrocarbylation
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and a hydrocarbyl group.
database_cross_reference: RSC:xp

arylation
type: Class
subclass of: hydrocarbylation
subclass of: Restriction
  on property: has_participant
  some values from: aryl group
definition: Formation of a covalent bond between a substrate and an aryl group.
has_exact_synonym: arylation
has_obo_namespace: RXNO
id: MOP:0000411

Axiom
annotated source: arylation
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and an aryl group.
database_cross_reference: RSC:xp

allylation
type: Class
subclass of: hydrocarbylation
definition: Formation of a covalent bond between a substrate and an allyl group.
has_exact_synonym: allylation
has_obo_namespace: RXNO
id: MOP:0000422
comment: has_participant: CHEBI:30361

Axiom
annotated source: allylation
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and an allyl group.
database_cross_reference: RSC:xp

organylation
type: Class
subclass of: formation of covalent bond with group
definition: Formation of a covalent bond between a substrate and an organyl group.
has_exact_synonym: organylation
has_obo_namespace: RXNO
id: MOP:0000458
comment: has_participant: CHEBI:33249

Axiom
annotated source: organylation
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and an organyl group.
database_cross_reference: RSC:xp

acylation
type: Class
subclass of: organylation
definition: Formation of a covalent bond between a substrate and an acyl group.
has_exact_synonym: acylation
has_obo_namespace: RXNO
id: MOP:0000479
comment: has_participant: CHEBI:22221

Axiom
annotated source: acylation
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and an acyl group.
database_cross_reference: RSC:xp

MOP_0000524
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: sulfonylation
deprecated: true

sulfonylation
type: Class
subclass of: formation of covalent bond with group
definition: Formation of a covalent bond between a substrate and a sulfonyl group.
has_alternative_id: MOP:0000524
has_exact_synonym: sulfonylation
has_obo_namespace: RXNO
id: MOP:0000539
comment: has_participant: CHEBI:51100; has_participant: CHEBI:29825

Axiom
annotated source: sulfonylation
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and a sulfonyl group.
database_cross_reference: RSC:xp

molecular process
type: Class
subclass of: process
definition: A process in which at least one of the participants is a molecule.
has_obo_namespace: RXNO
id: MOP:0000543
comment: TODO: needs work, formal definition, etc.

Axiom
annotated source: molecular process
annotated property: definition
annotated target: A process in which at least one of the participants is a molecule.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

halogenation
type: Class
subclass of: formation of covalent bond with group
definition: Formation of a covalent bond between a substrate and a halo group.
has_obo_namespace: RXNO
id: MOP:0000550
comment: has_participant: CHEBI:47854

Axiom
annotated source: halogenation
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and a halo group.
database_cross_reference: RSC:xp

imination
type: Class
subclass of: formation of covalent bond with nitrogen centre
definition: Formation of a covalent bond between a substrate and an imino group.
has_obo_namespace: RXNO
id: MOP:0000555
comment: has_participant: CHEBI:29342

Axiom
annotated source: imination
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and an imino group.
database_cross_reference: RSC:xp

nitration
type: Class
subclass of: formation of covalent bond with group
subclass of: Restriction
  on property: has_participant
  some values from: nitro group
definition: Formation of a covalent bond between a substrate and a nitro group.
has_obo_namespace: RXNO
id: MOP:0000556

Axiom
annotated source: nitration
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and a nitro group.
database_cross_reference: RSC:xp

cyclization
type: Class
subclass of: molecular process
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: cyclic compound
definition: Formation of a ring in a molecule from a chain by formation of a new bond.
has_exact_synonym: cyclisation
has_obo_namespace: RXNO
id: MOP:0000561

Axiom
annotated source: cyclization
annotated property: definition
annotated target: Formation of a ring in a molecule from a chain by formation of a new bond.
database_cross_reference: AU:C01494

cycloaddition
type: Class
subclass of: cyclization
definition: A molecular process where two or more unsaturated molecules or parts of the same molecule combine to form a cyclic adduct in which there is a net reduction of bond multiplicity.
has_alternative_id: RXNO:0000314
has_obo_namespace: RXNO
id: MOP:0000562

Axiom
annotated source: cycloaddition
annotated property: definition
annotated target: A molecular process where two or more unsaturated molecules or parts of the same molecule combine to form a cyclic adduct in which there is a net reduction of bond multiplicity.
database_cross_reference: AU:C01496

[2+2] cycloaddition
type: Class
subclass of: cycloaddition
definition: A cycloaddition in which each participant contributes two electrons to the transformation of reactants to products.
has_obo_namespace: RXNO
id: MOP:0000563

Axiom
annotated source: [2+2] cycloaddition
annotated property: definition
annotated target: A cycloaddition in which each participant contributes two electrons to the transformation of reactants to products.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

cycloelimination
type: Class
subclass of: molecular process
definition: A molecular process in which a cyclic system decomposes into two or more unsaturated molecules or parts of the same molecule and there is a net increase in bond multiplicity.
has_exact_synonym: cycloreversion
has_exact_synonym: retro-addition
has_exact_synonym: retrocycloaddition
has_obo_namespace: RXNO
id: MOP:0000564

Axiom
annotated source: cycloelimination
annotated property: definition
annotated target: A molecular process in which a cyclic system decomposes into two or more unsaturated molecules or parts of the same molecule and there is a net increase in bond multiplicity.
database_cross_reference: AU:C01496
database_cross_reference: AU:C01501

Axiom
annotated source: cycloelimination
annotated property: has_exact_synonym
annotated target: cycloreversion
database_cross_reference: AU:C01506

Axiom
annotated source: cycloelimination
annotated property: has_exact_synonym
annotated target: retrocycloaddition
database_cross_reference: AU:R05372

[4+2] cycloaddition
type: Class
subclass of: cycloaddition
subclass of: Restriction
  on property: realizes
  some values from: dienophilicity
definition: A cycloaddition in which one participant contributes four electrons and the other participant contributes two electrons to the transformation of reactants to products.
has_obo_namespace: RXNO
id: MOP:0000565

Axiom
annotated source: [4+2] cycloaddition
annotated property: definition
annotated target: A cycloaddition in which one participant contributes four electrons and the other participant contributes two electrons to the transformation of reactants to products.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

formation of covalent bond with group
type: Class
subclass of: molecular process
definition: Formation of a covalent bond between a substrate and a group.
created by: batchelorc
creation date: 2009-04-22T10:01:32Z
has_obo_namespace: RXNO
id: MOP:0000566

Axiom
annotated source: formation of covalent bond with group
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and a group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

breaking of covalent bond with group
type: Class
subclass of: molecular process
definition: Breaking of a covalent bond between a substrate and a group.
created by: batchelorc
creation date: 2009-04-30T02:24:32Z
has_obo_namespace: RXNO
id: MOP:0000567

Axiom
annotated source: breaking of covalent bond with group
annotated property: definition
annotated target: Breaking of a covalent bond between a substrate and a group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

oxidation
type: Class
subclass of: molecular process
definition: The complete, net removal of one or mole electrons from a molecular entity, corresponding to an increase in the oxidation number of any atom within any substrate.
created by: batchelorc
creation date: 2009-06-01T06:01:47Z
has_exact_synonym: de-electronation
has_obo_namespace: RXNO
id: MOP:0000568

Axiom
annotated source: oxidation
annotated property: definition
annotated target: The complete, net removal of one or mole electrons from a molecular entity, corresponding to an increase in the oxidation number of any atom within any substrate.
database_cross_reference: AU:O04362

reduction
type: Class
subclass of: molecular process
definition: The complete transfer of one or more electrons to a molecular entity.
created by: batchelorc
creation date: 2009-06-01T06:04:18Z
has_exact_synonym: electronation
has_obo_namespace: RXNO
id: MOP:0000569

Axiom
annotated source: reduction
annotated property: definition
annotated target: The complete transfer of one or more electrons to a molecular entity.
database_cross_reference: AU:R05222

electron attachment
type: Class
subclass of: reduction
definition: The transfer of an electron to a molecular entity, resulting in a molecular entity of increased negative charge.
created by: batchelorc
creation date: 2009-06-01T06:06:19Z
has_obo_namespace: RXNO
id: MOP:0000570

Axiom
annotated source: electron attachment
annotated property: definition
annotated target: The transfer of an electron to a molecular entity, resulting in a molecular entity of increased negative charge.
database_cross_reference: AU:E01979

aldehyde reduction
type: Class
subclass of: reduction
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: primary alcohol
subclass of: Restriction
  on property: has participant ceasing to exist
  some values from: aldehyde
definition: A reduction in which an aldehyde is reduced to form a primary alcohol.
created by: batchelorc
creation date: 2009-06-01T06:07:02Z
has_obo_namespace: RXNO
id: MOP:0000571

Axiom
annotated source: aldehyde reduction
annotated property: definition
annotated target: A reduction in which an aldehyde is reduced to form a primary alcohol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

alcohol oxidation
type: Class
subclass of: oxidation
subclass of: Restriction
  on property: has participant ceasing to exist
  some values from: alcohol
definition: An oxidation process where an alcohol is transformed into a carbonyl compound.
created by: batchelorc
creation date: 2009-06-01T06:10:35Z
has_obo_namespace: RXNO
id: MOP:0000572

Axiom
annotated source: alcohol oxidation
annotated property: definition
annotated target: An oxidation process where an alcohol is transformed into a carbonyl compound.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

primary alcohol oxidation to aldehyde
type: Class
subclass of: alcohol oxidation
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: aldehyde
subclass of: Restriction
  on property: has participant ceasing to exist
  some values from: primary alcohol
definition: An oxidation process where a primary alcohol is transformed into an aldehyde.
created by: batchelorc
creation date: 2009-06-01T06:10:59Z
has_obo_namespace: RXNO
id: MOP:0000573

Axiom
annotated source: primary alcohol oxidation to aldehyde
annotated property: definition
annotated target: An oxidation process where a primary alcohol is transformed into an aldehyde.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

secondary alcohol oxidation to ketone
type: Class
subclass of: alcohol oxidation
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: ketone
subclass of: Restriction
  on property: has participant ceasing to exist
  some values from: secondary alcohol
definition: An oxidation process where a secondary alcohol is transformed into a ketone.
created by: batchelorc
creation date: 2009-06-01T06:11:31Z
has_obo_namespace: RXNO
id: MOP:0000574

Axiom
annotated source: secondary alcohol oxidation to ketone
annotated property: definition
annotated target: An oxidation process where a secondary alcohol is transformed into a ketone.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

amine oxidation
type: Class
subclass of: oxidation at nitrogen
definition: An oxidation process where an amine is transformed into an imine.
created by: batchelorc
creation date: 2009-06-01T06:15:40Z
has_obo_namespace: RXNO
id: MOP:0000575

Axiom
annotated source: amine oxidation
annotated property: definition
annotated target: An oxidation process where an amine is transformed into an imine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

imine reduction
type: Class
subclass of: reduction
definition: A reduction process where an imine is transformed into an amine.
created by: batchelorc
creation date: 2009-06-01T06:19:21Z
has_obo_namespace: RXNO
id: MOP:0000576

Axiom
annotated source: imine reduction
annotated property: definition
annotated target: A reduction process where an imine is transformed into an amine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

ester reduction
type: Class
subclass of: reduction
subclass of: Restriction
  on property: has participant ceasing to exist
  some values from: carboxylic ester
definition: A reduction process where the oxidation state carbonyl carbon in the ester functionality is reduced.
created by: batchelorc
creation date: 2009-06-02T05:30:48Z
has_exact_synonym: reduction of ester
has_obo_namespace: RXNO
id: MOP:0000577

Axiom
annotated source: ester reduction
annotated property: definition
annotated target: A reduction process where the oxidation state carbonyl carbon in the ester functionality is reduced.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

ester reduction to aldehyde
type: Class
subclass of: ester reduction
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: aldehyde
definition: An ester reduction where the product is the corresponding aldehyde.
created by: batchelorc
creation date: 2009-06-02T05:31:49Z
has_exact_synonym: reduction of ester to aldehyde
has_exact_synonym: reduction of esters to aldehyde
has_obo_namespace: RXNO
id: MOP:0000578

Axiom
annotated source: ester reduction to aldehyde
annotated property: definition
annotated target: An ester reduction where the product is the corresponding aldehyde.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

ester reduction to primary alcohol
type: Class
subclass of: ester reduction
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: primary alcohol
definition: An ester reduction where the product is the corresponding primary alcohol.
created by: batchelorc
creation date: 2009-06-02T05:32:37Z
has_exact_synonym: reduction of ester to primary alcohol
has_exact_synonym: reduction of esters to primary alcohol
has_obo_namespace: RXNO
id: MOP:0000579

Axiom
annotated source: ester reduction to primary alcohol
annotated property: definition
annotated target: An ester reduction where the product is the corresponding primary alcohol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

ketone reduction
type: Class
subclass of: reduction
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: secondary alcohol
subclass of: Restriction
  on property: has participant ceasing to exist
  some values from: ketone
definition: A reduction process where a ketone is reduced to a secondary alcohol.
created by: batchelorc
creation date: 2009-06-02T05:35:42Z
has_exact_synonym: reduction of ketone
has_exact_synonym: reduction of ketones
has_obo_namespace: RXNO
id: MOP:0000580

Axiom
annotated source: ketone reduction
annotated property: definition
annotated target: A reduction process where a ketone is reduced to a secondary alcohol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

alkene oxidation
type: Class
subclass of: oxidation
definition: An oxidation process where the oxidation state of at least one doubly-bonded carbon atom increases.
created by: batchelorc
creation date: 2009-06-02T05:45:30Z
has_exact_synonym: olefin oxidation
has_obo_namespace: RXNO
id: MOP:0000581

Axiom
annotated source: alkene oxidation
annotated property: definition
annotated target: An oxidation process where the oxidation state of at least one doubly-bonded carbon atom increases.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

alkene oxidation to 1,2-diol
type: Class
subclass of: alkene oxidation
definition: An alkene oxidation where the product is the corresponding 1,2-diol.
created by: batchelorc
creation date: 2009-06-02T05:46:52Z
has_exact_synonym: alkene oxidation to glycol
has_exact_synonym: oxidation of alkene to 1,2-diol
has_exact_synonym: oxidation of alkenes to 1,2-diol
has_obo_namespace: RXNO
id: MOP:0000582

Axiom
annotated source: alkene oxidation to 1,2-diol
annotated property: definition
annotated target: An alkene oxidation where the product is the corresponding 1,2-diol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

alkene ozonolysis
type: Class
subclass of: alkene oxidative cleavage
definition: An alkene oxidation where the reagent is ozone and the product is the corresponding ozonide.
created by: batchelorc
creation date: 2009-06-02T05:48:42Z
has_exact_synonym: ozonolysis of alkene
has_exact_synonym: ozonolysis of alkenes
has_obo_namespace: RXNO
id: MOP:0000583

Axiom
annotated source: alkene ozonolysis
annotated property: definition
annotated target: An alkene oxidation where the reagent is ozone and the product is the corresponding ozonide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

primary alkene oxidation to carboxylic acid and carbon dioxide
type: Class
subclass of: alkene oxidative cleavage
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: carbon dioxide
definition: An alkene oxidation process where the reactant is a primary alkene and the products are carboxylic acid and carbon dioxide. This can be achieved with a warm, acidic solution of potassium permanganate.
created by: batchelorc
creation date: 2009-06-02T06:02:46Z
has_obo_namespace: RXNO
id: MOP:0000584

Axiom
annotated source: primary alkene oxidation to carboxylic acid and carbon dioxide
annotated property: definition
annotated target: An alkene oxidation process where the reactant is a primary alkene and the products are carboxylic acid and carbon dioxide. This can be achieved with a warm, acidic solution of potassium permanganate.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

tertiary alkene oxidation to carboxylic acid and ketone
type: Class
subclass of: alkene oxidative cleavage
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: ketone
definition: An alkene oxidation where the reactant is a tertiary alkene and the products are the corresponding carboxylic acid and ketone. This can be achieved with a warm, acidic solution of potassium permanganate.
created by: batchelorc
creation date: 2009-06-02T06:04:14Z
has_obo_namespace: RXNO
id: MOP:0000585

Axiom
annotated source: tertiary alkene oxidation to carboxylic acid and ketone
annotated property: definition
annotated target: An alkene oxidation where the reactant is a tertiary alkene and the products are the corresponding carboxylic acid and ketone. This can be achieved with a warm, acidic solution of potassium permanganate.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

secondary, non-terminal alkene oxidation to aldehydes
type: Class
subclass of: alkene oxidative cleavage
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: aldehyde
definition: An alkene oxidation process where the reactant is a secondary alkene and the products are the corresponding aldehydes. This can be achieved with warm, acidic potassium permanganate.
created by: batchelorc
creation date: 2009-06-02T06:06:23Z
has_obo_namespace: RXNO
id: MOP:0000586

Axiom
annotated source: secondary, non-terminal alkene oxidation to aldehydes
annotated property: definition
annotated target: An alkene oxidation process where the reactant is a secondary alkene and the products are the corresponding aldehydes. This can be achieved with warm, acidic potassium permanganate.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

secondary terminal alkene oxidation to ketone and carbon dioxide
type: Class
subclass of: alkene oxidative cleavage
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: carbon dioxide
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: ketone
definition: An alkene oxidation process where the reactant is a secondary terminal alkene and the products are carbon dioxide and the corresponding ketone. This can be achieved by warm, acidic potassium permanganate solution.
created by: batchelorc
creation date: 2009-06-02T06:07:44Z
has_obo_namespace: RXNO
id: MOP:0000587

Axiom
annotated source: secondary terminal alkene oxidation to ketone and carbon dioxide
annotated property: definition
annotated target: An alkene oxidation process where the reactant is a secondary terminal alkene and the products are carbon dioxide and the corresponding ketone. This can be achieved by warm, acidic potassium permanganate solution.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

quaternary alkene oxidation to ketones
type: Class
subclass of: alkene oxidative cleavage
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: ketone
definition: An alkene oxidation process where the reactant is a quaternary alkene and the products are the corresponding ketones.
created by: batchelorc
creation date: 2009-06-02T06:09:24Z
has_obo_namespace: RXNO
id: MOP:0000588

Axiom
annotated source: quaternary alkene oxidation to ketones
annotated property: definition
annotated target: An alkene oxidation process where the reactant is a quaternary alkene and the products are the corresponding ketones.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

hydrogenation
type: Class
subclass of: reduction
definition: A reduction process that involves addition of hydrogen atoms across a double bond.
created by: batchelorc
creation date: 2009-06-05T04:53:34Z
has_obo_namespace: RXNO
id: MOP:0000589

Axiom
annotated source: hydrogenation
annotated property: definition
annotated target: A reduction process that involves addition of hydrogen atoms across a double bond.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

pseudohalogenation
type: Class
subclass of: formation of covalent bond with group
subclass of: Restriction
  on property: has_participant
  some values from: pseudohalo group
definition: Formation of a covalent bond between a substrate and a pseudohalo group.
has_obo_namespace: RXNO
id: MOP:0000596

Axiom
annotated source: pseudohalogenation
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and a pseudohalo group.
database_cross_reference: RSC:xp

solvolysis
type: Class
subclass of: molecular process
definition: A molecular process where a molecule is broken up by reaction with a molecule that is part of the solvent material. It may be the primary constituent molecule of the solvent material (for example water, ethanol, ammonia) or its lyonium ion or lyate ion.
created by: batchelorc
creation date: 2009-09-16T11:11:24Z
has_obo_namespace: RXNO
id: MOP:0000618

Axiom
annotated source: solvolysis
annotated property: definition
annotated target: A molecular process where a molecule is broken up by reaction with a molecule that is part of the solvent material. It may be the primary constituent molecule of the solvent material (for example water, ethanol, ammonia) or its lyonium ion or lyate ion.
database_cross_reference: AU:S05762
database_cross_reference: https://orcid.org/0000-0001-5985-7429

hydrolysis
type: Class
subclass of: solvolysis
definition: A solvolysis reaction where the solvent material is water.
created by: batchelorc
creation date: 2009-09-16T11:13:21Z
has_obo_namespace: RXNO
id: MOP:0000619

Axiom
annotated source: hydrolysis
annotated property: definition
annotated target: A solvolysis reaction where the solvent material is water.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

condensation reaction
type: Class
subclass of: molecular process
definition: A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of a small molecule.
created by: batchelorc
creation date: 2009-09-16T11:30:32Z
has_alternative_id: RXNO:0000315
has_obo_namespace: RXNO
id: MOP:0000627

Axiom
annotated source: condensation reaction
annotated property: definition
annotated target: A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of a small molecule.
database_cross_reference: AU:C01238

molecular dehydration reaction
type: Class
subclass of: condensation reaction
definition: A condensation reaction where the small molecule produced is water.
created by: batchelorc
creation date: 2009-09-16T11:32:33Z
has_obo_namespace: RXNO
id: MOP:0000628

Axiom
annotated source: molecular dehydration reaction
annotated property: definition
annotated target: A condensation reaction where the small molecule produced is water.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

addition reaction
type: Class
subclass of: molecular process
definition: A reaction of two or more reacting molecular entities resulting in a single reaction product containing all atoms of all components with formation of two chemical bonds and a net reduction in bond multiplicity.
id: MOP:0000642

Axiom
annotated source: addition reaction
annotated property: definition
annotated target: A reaction of two or more reacting molecular entities resulting in a single reaction product containing all atoms of all components with formation of two chemical bonds and a net reduction in bond multiplicity.
database_cross_reference: https://doi.org/10.1351/goldbook.A00133

amination
type: Class
subclass of: formation of covalent bond with nitrogen centre
subclass of: Restriction
  on property: has_participant
  some values from: amino groups
definition: Formation of a covalent bond between a substrate and an amino group.
has_obo_namespace: RXNO
id: MOP:0000650

Axiom
annotated source: amination
annotated property: definition
annotated target: Formation of a covalent bond between a substrate and an amino group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

elimination reaction
type: Class
subclass of: molecular process
definition: A molecular process where two groups are lost with concomitant formation of an unsaturation in the molecule or formation of a new ring.
has_obo_namespace: RXNO
id: MOP:0000656

Axiom
annotated source: elimination reaction
annotated property: definition
annotated target: A molecular process where two groups are lost with concomitant formation of an unsaturation in the molecule or formation of a new ring.
database_cross_reference: doi:10.1351/goldbook.E02038

epoxidation
type: Class
subclass of: cyclization
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: epoxide
definition: A cyclisation that results in the formation of an epoxide.
has_obo_namespace: RXNO
id: MOP:0000671

Axiom
annotated source: epoxidation
annotated property: definition
annotated target: A cyclisation that results in the formation of an epoxide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

oxidation at sulfur
type: Class
subclass of: oxidation
definition: An oxidation process where the oxidation state of at least one sulfur atom increases.
has_obo_namespace: RXNO
id: MOP:0000705

Axiom
annotated source: oxidation at sulfur
annotated property: definition
annotated target: An oxidation process where the oxidation state of at least one sulfur atom increases.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

oxidation at nitrogen
type: Class
subclass of: oxidation
definition: An oxidation process where the oxidation state of at least one nitrogen atom increases.
has_obo_namespace: RXNO
id: MOP:0000706

Axiom
annotated source: oxidation at nitrogen
annotated property: definition
annotated target: An oxidation process where the oxidation state of at least one nitrogen atom increases.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

oxidation state
type: Class
subclass of: information content entity
definition: A formal account of the degree of oxidation of an atom.
database_cross_reference: http://goldbook.iupac.org/O04365.html
has_obo_namespace: RXNO
id: MOP:0000712
comment: It turns out to be formally defined, which makes our definitions a bit poor.

Axiom
annotated source: oxidation state
annotated property: definition
annotated target: A formal account of the degree of oxidation of an atom.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

carboxylation
type: Class
subclass of: acylation
subclass of: Restriction
  on property: has_participant
  some values from: carboxy group
definition: Formation of a covalent bond between a molecule and a carboxy group.
has_obo_namespace: RXNO
id: MOP:0000713

Axiom
annotated source: carboxylation
annotated property: definition
annotated target: Formation of a covalent bond between a molecule and a carboxy group.
database_cross_reference: RSC:xp

carbonyl oxidation to alkyne
type: Class
subclass of: oxidation
definition: Oxidation of a carbonyl group to an alkyne.
has_obo_namespace: RXNO
id: MOP:0000714

Axiom
annotated source: carbonyl oxidation to alkyne
annotated property: definition
annotated target: Oxidation of a carbonyl group to an alkyne.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

[3+2] cycloaddition
type: Class
subclass of: cycloaddition
definition: A cycloaddition in which one participant contributes three electrons and the other participant contributes two electrons to the transformation of reactants to products.
has_obo_namespace: RXNO
id: MOP:0000715

Axiom
annotated source: [3+2] cycloaddition
annotated property: definition
annotated target: A cycloaddition in which one participant contributes three electrons and the other participant contributes two electrons to the transformation of reactants to products.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

enolisation
type: Class
equivalent class: Class
  intersection of: molecular process
  intersection of: Restriction
    on property: realizes
    some values from: enolisability
subclass of: molecular process
subclass of: Restriction
  on property: realizes
  some values from: enolisability
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: enol
definition: Molecular process in which an aldehyde or ketone tautomerises to form an enol.
has_exact_synonym: enolization
has_obo_namespace: RXNO
id: MOP:0000716

Axiom
annotated source: enolisation
annotated property: definition
annotated target: Molecular process in which an aldehyde or ketone tautomerises to form an enol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

enolisability
type: Class
subclass of: disposition
definition: Disposition that is realised in the process of enolisation
has_obo_namespace: RXNO
id: MOP:0000717

Axiom
annotated source: enolisability
annotated property: definition
annotated target: Disposition that is realised in the process of enolisation
database_cross_reference: https://orcid.org/0000-0001-5985-7429

enolisable carbonyl compound
type: Class
equivalent class: Class
  intersection of: carbonyl compound
  intersection of: Restriction
    on property: has disposition at all times
    some values from: enolisability
subclass of: carbonyl compound
subclass of: Restriction
  on property: has disposition at all times
  some values from: enolisability
definition: A carbonyl compound that bears the disposition to be enolised.
has_obo_namespace: RXNO
id: MOP:0000718
comment: this surely belongs in ChEBI but put it here pro tem

Axiom
annotated source: enolisable carbonyl compound
annotated property: definition
annotated target: A carbonyl compound that bears the disposition to be enolised.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

O-dealkylation
type: Class
subclass of: dealkylation
definition: Breaking of a covalent bond between an alkyl group and an oxygen atom.
has_obo_namespace: RXNO
id: MOP:0000719

Axiom
annotated source: O-dealkylation
annotated property: definition
annotated target: Breaking of a covalent bond between an alkyl group and an oxygen atom.
database_cross_reference: RSC:xp

[2+2+1] cycloaddition
type: Class
subclass of: cycloaddition
definition: A cycloaddition in which two participants contribute two electrons and the other participant contributes one electron to the transformation of reactants to products.
has_obo_namespace: RXNO
id: MOP:0000720

Axiom
annotated source: [2+2+1] cycloaddition
annotated property: definition
annotated target: A cycloaddition in which two participants contribute two electrons and the other participant contributes one electron to the transformation of reactants to products.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

[3,3]-sigmatropic rearrangement
type: Class
subclass of: molecular process
has_alternative_id: RXNO:0000027
has_obo_namespace: RXNO
id: MOP:0000721
comment: This term was obsoleted from the RXNO namespace and transferred to MOP because it is a process identifiable by its mechanism rather than the intention of the experimenter.

decarboxylative condensation
type: Class
subclass of: condensation reaction
subclass of: Restriction
  on property: has_part
  some values from: decarboxylation
definition: A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of a carbon dioxide molecule.
created by: batchelorc
creation date: 2014-03-05T10:00:00Z
has_obo_namespace: RXNO
id: MOP:0000722

Axiom
annotated source: decarboxylative condensation
annotated property: definition
annotated target: A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of a carbon dioxide molecule.
database_cross_reference: RSC:xp

deethanolative condensation
type: Class
subclass of: dealcoholative condensation
definition: A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of an ethanol molecule.
created by: batchelorc
creation date: 2014-03-05T10:00:00Z
has_obo_namespace: RXNO
id: MOP:0000723

Axiom
annotated source: deethanolative condensation
annotated property: definition
annotated target: A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of an ethanol molecule.
database_cross_reference: RSC:xp

Brønsted acid catalysis
type: Class
subclass of: acid catalysis
created by: batchelorc
creation date: 2014-04-09T10:00:00Z
has_obo_namespace: RXNO
id: MOP:0000730

base catalysis
type: Class
equivalent class: Class
  union of: Lewis base catalysis
  union of: Brønsted base catalysis
subclass of: molecular process
created by: batchelorc
creation date: 2014-04-09T10:00:00Z
has_obo_namespace: RXNO
id: MOP:0000731

hydron donation
type: Class
subclass of: molecular process
subclass of: Restriction
  on property: realizes
  some values from: Brønsted acid
created by: batchelorc
creation date: 2014-04-09T10:00:00Z
has_obo_namespace: RXNO
id: MOP:0000732

accepting an electron pair in Lewis adduct formation
type: Class
subclass of: molecular process
subclass of: Restriction
  on property: realizes
  some values from: Lewis acid
created by: batchelorc
creation date: 2014-04-09T10:00:00Z
has_obo_namespace: RXNO
id: MOP:0000733

Lewis acid catalysis
type: Class
subclass of: acid catalysis
created by: batchelorc
creation date: 2014-04-09T10:00:00Z
has_obo_namespace: RXNO
id: MOP:0000734

Lewis base catalysis
type: Class
subclass of: base catalysis
created by: batchelorc
creation date: 2014-04-09T10:00:00Z
has_obo_namespace: RXNO
id: MOP:0000735

Brønsted base catalysis
type: Class
subclass of: base catalysis
subclass of: Restriction
  on property: has_part
  some values from: accepting a hydron
created by: batchelorc
creation date: 2014-04-09T10:00:00Z
has_obo_namespace: RXNO
id: MOP:0000736

accepting a hydron
type: Class
subclass of: molecular process
subclass of: Restriction
  on property: realizes
  some values from: Brønsted base
created by: batchelorc
creation date: 2014-04-09T10:00:00Z
has_obo_namespace: RXNO
id: MOP:0000737

electron pair donation in Lewis adduct formation
type: Class
subclass of: molecular process
subclass of: Restriction
  on property: realizes
  some values from: Lewis base
created by: batchelorc
creation date: 2014-04-09T10:00:00Z
has_obo_namespace: RXNO
id: MOP:0000738

Lewis adduct formation
type: Class
subclass of: molecular process
subclass of: Restriction
  on property: has_part
  some values from: accepting an electron pair in Lewis adduct formation
subclass of: Restriction
  on property: has_part
  some values from: electron pair donation in Lewis adduct formation
has_obo_namespace: RXNO
id: MOP:0000739

acid catalysis
type: Class
equivalent class: Class
  union of: Brønsted acid catalysis
  union of: Lewis acid catalysis
subclass of: molecular process
definition: Catalysis of a reaction where the catalyst either donates a hydron or accepts an electron pair.
has_obo_namespace: RXNO
id: MOP:0000740

Axiom
annotated source: acid catalysis
annotated property: definition
annotated target: Catalysis of a reaction where the catalyst either donates a hydron or accepts an electron pair.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

substitution reaction
type: Class
subclass of: molecular process
definition: A reaction in which one singly-bonded group, but not the hydrogen atom, is replaced by another singly-bonded group.
has_alternative_id: RXNO:0000019
has_obo_namespace: RXNO
id: MOP:0000790
comment: The Gold Book says hydrogen atoms count, but this differs from everyone's intuition. See http://goldbook.iupac.org/S06078.html

Axiom
annotated source: substitution reaction
annotated property: definition
annotated target: A reaction in which one singly-bonded group, but not the hydrogen atom, is replaced by another singly-bonded group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

aromatic substitution
type: Class
subclass of: substitution reaction
definition: A substitution reaction in which one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent.
has_alternative_id: RXNO:0000020
has_obo_namespace: RXNO
id: MOP:0000791

Axiom
annotated source: aromatic substitution
annotated property: definition
annotated target: A substitution reaction in which one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

allylic rearrangement
type: Class
subclass of: substitution reaction
definition: A substitution reaction in an allylic system with concomitant migration of the allyl double bond.
has_alternative_id: RXNO:0000033
has_obo_namespace: RXNO
id: MOP:0000792

Axiom
annotated source: allylic rearrangement
annotated property: definition
annotated target: A substitution reaction in an allylic system with concomitant migration of the allyl double bond.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

N-substitution
type: Class
subclass of: substitution reaction
definition: A substitution reaction where the reactive centre is a nitrogen atom.
has_alternative_id: RXNO:0000319
has_obo_namespace: RXNO
id: MOP:0000793

Axiom
annotated source: N-substitution
annotated property: definition
annotated target: A substitution reaction where the reactive centre is a nitrogen atom.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

O-substitution
type: Class
subclass of: substitution reaction
definition: A substitution reaction where the reactive centre is an oxygen atom.
has_alternative_id: RXNO:0000318
database_cross_reference: NAMERXN:1.7
has_obo_namespace: RXNO
id: MOP:0000794

Axiom
annotated source: O-substitution
annotated property: definition
annotated target: A substitution reaction where the reactive centre is an oxygen atom.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

S-substitution
type: Class
subclass of: substitution reaction
definition: A substitution reaction where the reactive centre is a sulfur atom.
created by: batchelorc
creation date: 2012-03-22T12:22:59Z
has_alternative_id: RXNO:0000336
database_cross_reference: NAMERXN:1.8
has_obo_namespace: RXNO
id: MOP:0000795

Axiom
annotated source: S-substitution
annotated property: definition
annotated target: A substitution reaction where the reactive centre is a sulfur atom.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

formation of covalent bond with nitrogen centre
type: Class
subclass of: formation of covalent bond with group
definition: Formation of a covalent bond with a group where the free valence is on a nitrogen centre.
has_obo_namespace: RXNO
id: MOP:0000802

Axiom
annotated source: formation of covalent bond with nitrogen centre
annotated property: definition
annotated target: Formation of a covalent bond with a group where the free valence is on a nitrogen centre.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

dealcoholative condensation
type: Class
subclass of: condensation reaction
definition: A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of an alcohol molecule.
has_obo_namespace: RXNO
id: MOP:0000825

Axiom
annotated source: dealcoholative condensation
annotated property: definition
annotated target: A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of an alcohol molecule.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

dienophilicity
type: Class
subclass of: disposition
definition: A disposition which is realised in a [4+2] reaction with a double-bonded system.
database_cross_reference: http://goldbook.iupac.org/D01700.html
has_obo_namespace: RXNO
id: MOP:0000826

Axiom
annotated source: dienophilicity
annotated property: definition
annotated target: A disposition which is realised in a [4+2] reaction with a double-bonded system.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

dealkylation
type: Class
subclass of: deorganylation
definition: Breaking of a covalent bond between an alkyl group and a substrate.
has_obo_namespace: RXNO
id: MOP:0001369

Axiom
annotated source: dealkylation
annotated property: definition
annotated target: Breaking of a covalent bond between an alkyl group and a substrate.
database_cross_reference: RSC:xp

deorganylation
type: Class
subclass of: breaking of covalent bond with group
definition: Breaking of a covalent bond between a substrate and an organyl group.
has_obo_namespace: RXNO
id: MOP:0001458
comment: has_participant: CHEBI:33249

Axiom
annotated source: deorganylation
annotated property: definition
annotated target: Breaking of a covalent bond between a substrate and an organyl group.
database_cross_reference: RSC:xp

dehalogenation
type: Class
subclass of: breaking of covalent bond with group
definition: Breaking of a covalent bond between a substrate and a halo group.
has_obo_namespace: RXNO
id: MOP:0001550
comment: has_participant: CHEBI:47854

Axiom
annotated source: dehalogenation
annotated property: definition
annotated target: Breaking of a covalent bond between a substrate and a halo group.
database_cross_reference: RSC:xp

decarboxylation
type: Class
subclass of: deorganylation
subclass of: Restriction
  on property: has_participant
  some values from: carboxy group
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: carbon dioxide
definition: Breaking of a covalent bond between a molecule and a carboxy group.
has_obo_namespace: RXNO
id: MOP:0001713

Axiom
annotated source: decarboxylation
annotated property: definition
annotated target: Breaking of a covalent bond between a molecule and a carboxy group.
database_cross_reference: RSC:xp

N-methylation
type: Class
subclass of: methylation
definition: Formation of a covalent bond between a nitrogen atom in a substrate and a methyl group.
has_obo_namespace: RXNO
id: MOP:0002364
comment: has_participant: CHEBI:32875

Axiom
annotated source: N-methylation
annotated property: definition
annotated target: Formation of a covalent bond between a nitrogen atom in a substrate and a methyl group.
database_cross_reference: RSC:xp

N-alkylation
type: Class
subclass of: alkylation
definition: Formation of a covalent bond between a nitrogen atom in a substrate and an alkyl group.
has_obo_namespace: RXNO
id: MOP:0002369
comment: has_participant: CHEBI:22323

Axiom
annotated source: N-alkylation
annotated property: definition
annotated target: Formation of a covalent bond between a nitrogen atom in a substrate and an alkyl group.
database_cross_reference: RSC:xp

N-arylation
type: Class
subclass of: arylation
subclass of: Restriction
  on property: has_participant
  some values from: aryl group
definition: Formation of a covalent bond between a nitrogen atom in a substrate and an aryl group.
has_obo_namespace: RXNO
id: MOP:0002411

Axiom
annotated source: N-arylation
annotated property: definition
annotated target: Formation of a covalent bond between a nitrogen atom in a substrate and an aryl group.
database_cross_reference: RSC:xp

N-acylation
type: Class
subclass of: acylation
definition: Formation of a covalent bond between a nitrogen atom in a substrate and an acyl group.
has_obo_namespace: RXNO
id: MOP:0002479
comment: has_participant: CHEBI:22221

Axiom
annotated source: N-acylation
annotated property: definition
annotated target: Formation of a covalent bond between a nitrogen atom in a substrate and an acyl group.
database_cross_reference: RSC:xp

N-sulfonylation
type: Class
subclass of: sulfonylation
definition: Formation of a covalent bond between a nitrogen atom in a substrate and a sulfonyl group.
has_obo_namespace: RXNO
id: MOP:0002524
comment: has_participant: CHEBI:29825

Axiom
annotated source: N-sulfonylation
annotated property: definition
annotated target: Formation of a covalent bond between a nitrogen atom in a substrate and a sulfonyl group.
database_cross_reference: RSC:xp

O-silylation
type: Class
subclass of: silylation
definition: Formation of a covalent bond between an oxygen atom in a substrate and a silyl group.
has_obo_namespace: RXNO
id: MOP:0003339
comment: has_participant: CHEBI:30541

Axiom
annotated source: O-silylation
annotated property: definition
annotated target: Formation of a covalent bond between an oxygen atom in a substrate and a silyl group.
database_cross_reference: RSC:xp

O-acylation
type: Class
subclass of: acylation
definition: Formation of a covalent bond between an oxygen atom in a substrate and an acyl group.
has_obo_namespace: RXNO
id: MOP:0003479
comment: has_participant: CHEBI:22221

Axiom
annotated source: O-acylation
annotated property: definition
annotated target: Formation of a covalent bond between an oxygen atom in a substrate and an acyl group.
database_cross_reference: RSC:xp

O-sulfonylation
type: Class
subclass of: sulfonylation
definition: Formation of a covalent bond between an oxygen atom in a substrate and a sulfonyl group.
has_obo_namespace: RXNO
id: MOP:0003524
comment: has_participant: CHEBI:29825

Axiom
annotated source: O-sulfonylation
annotated property: definition
annotated target: Formation of a covalent bond between an oxygen atom in a substrate and a sulfonyl group.
database_cross_reference: RSC:xp

P-alkylation
type: Class
subclass of: alkylation
definition: The formation of a covalent bond between a phosphorus atom and an alkyl group.
has_obo_namespace: RXNO
id: MOP:0006369

Axiom
annotated source: P-alkylation
annotated property: definition
annotated target: The formation of a covalent bond between a phosphorus atom and an alkyl group.
database_cross_reference: RSC:xp

planned process
type: Class
subclass of: process
has_obo_namespace: RXNO
id: OBI:0000011

molecular skeleton joining reaction
type: Class
equivalent class: Class
  intersection of: carbon-carbon coupling reaction
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: molecular skeleton joining objective
subclass of: planned reaction step
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular skeleton joining objective
definition: A reaction where the number of atoms in the molecular skeleton increases.
has_exact_synonym: coupling reaction
has_obo_namespace: RXNO
id: RXNO:0000000

Axiom
annotated source: molecular skeleton joining reaction
annotated property: definition
annotated target: A reaction where the number of atoms in the molecular skeleton increases.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

planned reaction step
type: Class
equivalent class: Class
  intersection of: planned process
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: molecular transformation objective
subclass of: planned process
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular transformation objective
subclass of: Restriction
  on property: part_of
  some values from: planned synthesis
definition: A molecular process with which the experimenters aim to achieve a particular molecular transformation.
has_obo_namespace: RXNO
id: RXNO:0000001

Axiom
annotated source: planned reaction step
annotated property: definition
annotated target: A molecular process with which the experimenters aim to achieve a particular molecular transformation.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

carbon-carbon coupling reaction
type: Class
subclass of: molecular process
definition: A reaction where a bond is formed between two carbon atoms.
database_cross_reference: NAMERXN:3
has_obo_namespace: RXNO
id: RXNO:0000002

Axiom
annotated source: carbon-carbon coupling reaction
annotated property: definition
annotated target: A reaction where a bond is formed between two carbon atoms.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Perkin reaction
type: Class
subclass of: aldol condensation
subclass of: Restriction
  on property: has specified product
  some values from: cinnamic acids
subclass of: Restriction
  on property: has specified reactant
  some values from: arenecarbaldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: acid anhydride
definition: An aldol condensation where an aryl aldehyde reacts with an acid anhydride to form a cinnamic acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r327/
database_cross_reference: https://www.wikidata.org/wiki/Q898605
has_obo_namespace: RXNO
id: RXNO:0000003

Axiom
annotated source: Perkin reaction
annotated property: definition
annotated target: An aldol condensation where an aryl aldehyde reacts with an acid anhydride to form a cinnamic acid.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

obsolete: ring reaction
type: Class
definition: A reaction in which the number of atoms in any ring changes between the reactant and the products.
has_obo_namespace: RXNO
id: RXNO:0000004
comment: This term was obsoleted because it was a grouping term that wasn't much help.
deprecated: true

Axiom
annotated source: obsolete: ring reaction
annotated property: definition
annotated target: A reaction in which the number of atoms in any ring changes between the reactant and the products.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

ring formation reaction step
type: Class
equivalent class: Class
  intersection of: molecular process
  intersection of: Restriction
    on property: has specified product
    some values from: cyclic compound
subclass of: cyclization
subclass of: planned reaction step
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular ring formation objective
subclass of: Restriction
  on property: has specified product
  some values from: cyclic compound
definition: A planned reaction step where the product contains a ring that was not in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000005

Axiom
annotated source: ring formation reaction step
annotated property: definition
annotated target: A planned reaction step where the product contains a ring that was not in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Diels-Alder reaction
type: Class
subclass of: [4+2] cycloaddition
definition: A [4+2] cycloaddition reaction where a diene reacts with a compound containing a double or triple bond (a dienophile) to form an unsaturated six-membered ring compound.
database_cross_reference: NAMERXN:3.11.3
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r109/
database_cross_reference: https://www.wikidata.org/wiki/Q375669
has_exact_synonym: Diels-Alder coupling
has_exact_synonym: Diels-Alder cycloaddition
has_obo_namespace: RXNO
id: RXNO:0000006

Axiom
annotated source: Diels-Alder reaction
annotated property: definition
annotated target: A [4+2] cycloaddition reaction where a diene reacts with a compound containing a double or triple bond (a dienophile) to form an unsaturated six-membered ring compound.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

ene reaction
type: Class
subclass of: molecular skeleton joining reaction
definition: A joining reaction where an alkene with an allylic hydrogen reacts with a compound containing a multiple bond (an enophile) to form a substituted alkene.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r129/
database_cross_reference: https://www.wikidata.org/wiki/Q26469
has_obo_namespace: RXNO
id: RXNO:0000007

Axiom
annotated source: ene reaction
annotated property: definition
annotated target: A joining reaction where an alkene with an allylic hydrogen reacts with a compound containing a multiple bond (an enophile) to form a substituted alkene.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

conjugate addition
type: Class
subclass of: molecular skeleton joining reaction
definition: A joining reaction where a nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond).
database_cross_reference: https://www.wikidata.org/wiki/Q2181524
has_exact_synonym: nucleophilic conjugate addition
has_obo_namespace: RXNO
id: RXNO:0000008

Axiom
annotated source: conjugate addition
annotated property: definition
annotated target: A joining reaction where a nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond).
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

Michael addition
type: Class
subclass of: conjugate addition
definition: A conjugate addition reaction where a carbon nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond).
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r281/
database_cross_reference: https://www.wikidata.org/wiki/Q642233
has_exact_synonym: Michael reaction
has_obo_namespace: RXNO
id: RXNO:0000009

Axiom
annotated source: Michael addition
annotated property: definition
annotated target: A conjugate addition reaction where a carbon nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond).
database_cross_reference: RSC:db

functional modification
type: Class
equivalent class: Class
  intersection of: planned reaction step
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: functional modification objective
subclass of: planned reaction step
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: functional modification objective
definition: A reaction where the number of atoms in the skeleton, and their connectivity, remain the same.
has_obo_namespace: RXNO
id: RXNO:0000010

Axiom
annotated source: functional modification
annotated property: definition
annotated target: A reaction where the number of atoms in the skeleton, and their connectivity, remain the same.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

functional group modification
type: Class
equivalent class: Class
  intersection of: functional modification
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: functional group modification objective
subclass of: functional modification
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: functional group modification objective
definition: A reaction in which a functional group undergoes a change that does not affect the number of atoms in (or connectivity of) the skeleton of the molecule.
database_cross_reference: NAMERXN:9
has_obo_namespace: RXNO
id: RXNO:0000011

Axiom
annotated source: functional group modification
annotated property: definition
annotated target: A reaction in which a functional group undergoes a change that does not affect the number of atoms in (or connectivity of) the skeleton of the molecule.
database_cross_reference: rsc:db

functional group oxidation
type: Class
equivalent class: Class
  intersection of: functional group modification
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: functional oxidation objective
subclass of: oxidation
subclass of: functional group modification
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: functional oxidation objective
definition: A functional group modification reaction where a functional group is oxidised.
has_obo_namespace: RXNO
id: RXNO:0000012

Axiom
annotated source: functional group oxidation
annotated property: definition
annotated target: A functional group modification reaction where a functional group is oxidised.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

diazotisation
type: Class
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified reactant
  some values from: aromatic amine
definition: A functional group oxidation where an aromatic amine is transformed into an aromatic diazonium salt.
has_exact_synonym: diazotization
has_obo_namespace: RXNO
id: RXNO:0000013

Axiom
annotated source: diazotisation
annotated property: definition
annotated target: A functional group oxidation where an aromatic amine is transformed into an aromatic diazonium salt.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Grignard reaction
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: organomagnesium halide
definition: A carbon-carbon coupling reaction where a Grignard reagent reacts with a compound containing an electrophilic carbon atom. A Grignard reagent is a magnesium-stabilised carbon nucleophile. An aldehyde leads to a secondary alcohol, a ketone leads to a tertiary alcohol, an ester leads to a ketone and a nitrile leads to a ketone.
database_cross_reference: NAMERXN:3.7
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r177/
database_cross_reference: https://www.wikidata.org/wiki/Q337748
has_obo_namespace: RXNO
id: RXNO:0000014

Axiom
annotated source: Grignard reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction where a Grignard reagent reacts with a compound containing an electrophilic carbon atom. A Grignard reagent is a magnesium-stabilised carbon nucleophile. An aldehyde leads to a secondary alcohol, a ketone leads to a tertiary alcohol, an ester leads to a ketone and a nitrile leads to a ketone.
database_cross_reference: RSC:db

Wittig reaction
type: Class
subclass of: olefination
subclass of: Restriction
  on property: has specified product
  some values from: olefin
subclass of: Restriction
  on property: has specified reactant
  some values from: phosphonium ylide
definition: A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give an alkene.
database_cross_reference: NAMERXN:3.8
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r468/
database_cross_reference: https://www.wikidata.org/wiki/Q909735
has_exact_synonym: Wittig condensation
has_exact_synonym: Wittig olefination
has_obo_namespace: RXNO
id: RXNO:0000015

Axiom
annotated source: Wittig reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give an alkene.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

aldol addition
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified product
  some values from: beta-hydroxy ketone
definition: A carbon-carbon coupling reaction where an enol or enolate reacts with a carbonyl compound to form a beta-hydroxy ketone. The name comes from aldehyde + alcohol.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r4/
database_cross_reference: https://www.wikidata.org/wiki/Q494392
has_exact_synonym: aldol reaction
has_obo_namespace: RXNO
id: RXNO:0000016

Axiom
annotated source: aldol addition
annotated property: definition
annotated target: A carbon-carbon coupling reaction where an enol or enolate reacts with a carbonyl compound to form a beta-hydroxy ketone. The name comes from aldehyde + alcohol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

aldol condensation
type: Class
subclass of: molecular dehydration reaction
subclass of: aldol addition
subclass of: Restriction
  on property: has specified product
  some values from: alpha,beta-unsaturated ketone
definition: An aldol addition where an enol or enolate reacts with a carbonyl compound to form an alpha,beta-unsaturated ketone.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r4/
database_cross_reference: https://www.wikidata.org/wiki/Q1027170
has_obo_namespace: RXNO
id: RXNO:0000017

Axiom
annotated source: aldol condensation
annotated property: definition
annotated target: An aldol addition where an enol or enolate reacts with a carbonyl compound to form an alpha,beta-unsaturated ketone.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

1,3-dipolar cycloaddition
type: Class
subclass of: cycloaddition
definition: A ring formation reaction where a 1,3-dipolar compound reacts with an alkene or alkyne to form a five-membered ring compound.
database_cross_reference: https://www.wikidata.org/wiki/Q902907
has_narrow_synonym: Huisgen cycloaddition
has_narrow_synonym: Huisgen reaction
has_narrow_synonym: Huisgen's 1,3-dipolar cycloaddition
has_obo_namespace: RXNO
id: RXNO:0000018

Axiom
annotated source: 1,3-dipolar cycloaddition
annotated property: definition
annotated target: A ring formation reaction where a 1,3-dipolar compound reacts with an alkene or alkyne to form a five-membered ring compound.
database_cross_reference: RSC:db

RXNO_0000019
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: substitution reaction
deprecated: true

RXNO_0000020
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: aromatic substitution
deprecated: true

Sandmeyer reaction
type: Class
equivalent class: Class
  union of: Sandmeyer halogenation
  union of: Sandmeyer pseudohalogenation
subclass of: aromatic substitution step
definition: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide or pseudohalide to form an aromatic halide or pseudohalide.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r386/
database_cross_reference: https://www.wikidata.org/wiki/Q898821
has_obo_namespace: RXNO
id: RXNO:0000021

Axiom
annotated source: Sandmeyer reaction
annotated property: definition
annotated target: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide or pseudohalide to form an aromatic halide or pseudohalide.
database_cross_reference: RSC:db

Gattermann halogenation
type: Class
equivalent class: Class
  union of: Gattermann chlorination
  union of: Gattermann bromination
subclass of: halogenation
subclass of: aromatic substitution step
subclass of: Restriction
  on property: has_catalyst
  some values from: copper atom
definition: An aromatic substitution reaction where an aryl diazonium salt reacts with copper powder and hydrochloric acid or hydrobromic acid to form an aromatic chloride or bromide.
has_obo_namespace: RXNO
has_related_synonym: Gattermann reaction
id: RXNO:0000022
comment: This is also sometimes known as the Gattermann reaction. Also doesn't work to make fluorides or iodides.

Axiom
annotated source: Gattermann halogenation
annotated property: definition
annotated target: An aromatic substitution reaction where an aryl diazonium salt reacts with copper powder and hydrochloric acid or hydrobromic acid to form an aromatic chloride or bromide.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Koerner-Contardi reaction
type: Class
subclass of: aromatic substitution step
definition: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) halide to form an aromatic halide.
has_obo_namespace: RXNO
id: RXNO:0000023

Axiom
annotated source: Koerner-Contardi reaction
annotated property: definition
annotated target: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) halide to form an aromatic halide.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Heck reaction
type: Class
equivalent class: Class
  intersection of: Heck-type reaction
  intersection of: Restriction
    on property: has_catalyst
    some values from: palladium atom
definition: A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium. It is stereospecific.
database_cross_reference: NAMERXN:3.2
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r192/
database_cross_reference: https://www.wikidata.org/wiki/Q899916
has_exact_synonym: Heck-Mizoroki reaction
has_exact_synonym: Mizoroki-Heck reaction
has_obo_namespace: RXNO
id: RXNO:0000024
comment: This usually produces the trans-olefin rather than the cis-. ALSO Merck Index gives a non-terminal example.

Axiom
annotated source: Heck reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium. It is stereospecific.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429

rearrangement step
type: Class
equivalent class: Class
  intersection of: planned reaction step
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: molecular rearrangement objective
subclass of: planned reaction step
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular rearrangement objective
definition: A reaction which preserves the number of rings and number of skeletal atoms and in which the molecule rearranges so that one or more atoms or groups of atoms move from one atom to another.
has_obo_namespace: RXNO
id: RXNO:0000025

Axiom
annotated source: rearrangement step
annotated property: definition
annotated target: A reaction which preserves the number of rings and number of skeletal atoms and in which the molecule rearranges so that one or more atoms or groups of atoms move from one atom to another.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Beckmann rearrangement
type: Class
subclass of: rearrangement step
subclass of: Restriction
  on property: has specified product
  some values from: amide
subclass of: Restriction
  on property: has specified reactant
  some values from: oxime
definition: A rearrangement where an oxime rearranges to form an amide. Often there is selective migration of one group.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r29/
database_cross_reference: https://www.wikidata.org/wiki/Q813746
has_obo_namespace: RXNO
id: RXNO:0000026

Axiom
annotated source: Beckmann rearrangement
annotated property: definition
annotated target: A rearrangement where an oxime rearranges to form an amide. Often there is selective migration of one group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

RXNO_0000027
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: [3,3]-sigmatropic rearrangement
deprecated: true

Cope rearrangement
type: Class
subclass of: [3,3]-sigmatropic rearrangement
subclass of: rearrangement step
definition: A [3,3]-sigmatropic rearrangement where a 1,5-hexadiene rearranges to form a 1,5-hexadiene.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r86/
database_cross_reference: https://www.wikidata.org/wiki/Q905087
has_obo_namespace: RXNO
id: RXNO:0000028

Axiom
annotated source: Cope rearrangement
annotated property: definition
annotated target: A [3,3]-sigmatropic rearrangement where a 1,5-hexadiene rearranges to form a 1,5-hexadiene.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

oxy-Cope rearrangement
type: Class
subclass of: [3,3]-sigmatropic rearrangement
subclass of: rearrangement step
definition: A [3,3]-sigmatropic rearrangement of a 3-hydroxy-1,5-hexadiene rearranges to form a 5,6-unsaturated carbonyl compound.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r86/
database_cross_reference: https://www.wikidata.org/wiki/Q25326942
has_obo_namespace: RXNO
id: RXNO:0000029

Axiom
annotated source: oxy-Cope rearrangement
annotated property: definition
annotated target: A [3,3]-sigmatropic rearrangement of a 3-hydroxy-1,5-hexadiene rearranges to form a 5,6-unsaturated carbonyl compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

molecular skeleton insertion reaction
type: Class
equivalent class: Class
  intersection of: molecular skeleton joining reaction
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: molecular skeleton insertion objective
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular skeleton insertion objective
definition: A joining reaction in which one or more atoms are added to the middle of a chain.
has_obo_namespace: RXNO
id: RXNO:0000030

Axiom
annotated source: molecular skeleton insertion reaction
annotated property: definition
annotated target: A joining reaction in which one or more atoms are added to the middle of a chain.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Baeyer-Villiger oxidation
type: Class
subclass of: molecular skeleton insertion reaction
subclass of: Restriction
  on property: has specified product
  some values from: carboxylic ester
subclass of: Restriction
  on property: has specified reactant
  some values from: ketone
definition: A reaction of a ketone to give an ester, in which an alkyl, benzyl or phenyl group migrates from one of the alpha-carbon centres to an adjacent oxygen, displacing an oxygen-based leaving group; the result is a formal insertion of an oxygen atom. The reaction also works with aldehydes, giving the corresponding carboxylic acid. The term "Baeyer-Villiger rearrangement" may occasionally be used in a mechanistic sense to refer specificially to the actual rearrangement step.
has_alternative_id: RXNO:0000190
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r13/
database_cross_reference: https://www.wikidata.org/wiki/Q182033
has_exact_synonym: B-V reaction
has_exact_synonym: Baeyer-Villiger oxidative rearrangement
has_exact_synonym: Baeyer-Villiger reaction
has_obo_namespace: RXNO
has_related_synonym: Baeyer-Villiger rearrangement
id: RXNO:0000031

Axiom
annotated source: Baeyer-Villiger oxidation
annotated property: definition
annotated target: A reaction of a ketone to give an ester, in which an alkyl, benzyl or phenyl group migrates from one of the alpha-carbon centres to an adjacent oxygen, displacing an oxygen-based leaving group; the result is a formal insertion of an oxygen atom. The reaction also works with aldehydes, giving the corresponding carboxylic acid. The term "Baeyer-Villiger rearrangement" may occasionally be used in a mechanistic sense to refer specificially to the actual rearrangement step.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

Mannich reaction
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: enolisable carbonyl compound
definition: A carbon-carbon coupling reaction where ammonia or an amine reacts with a non-enolisable aldehyde, often methanal, and an enolisable carbonyl compound to form a beta-amino carbonyl compound.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r265/
database_cross_reference: https://www.wikidata.org/wiki/Q183055
has_obo_namespace: RXNO
id: RXNO:0000032

Axiom
annotated source: Mannich reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction where ammonia or an amine reacts with a non-enolisable aldehyde, often methanal, and an enolisable carbonyl compound to form a beta-amino carbonyl compound.
database_cross_reference: RSC:db

RXNO_0000033
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: allylic rearrangement
deprecated: true

Mitsunobu reaction
type: Class
subclass of: substitution step
subclass of: Restriction
  on property: has specified reactant
  some values from: alcohol
definition: A substitution where an alcohol is converted into something else. Typical reagents are a dialkyl azodicarboxylate and a triarylphosphine. The alcohol stereocentre is inverted.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r287/
database_cross_reference: https://www.wikidata.org/wiki/Q899062
has_obo_namespace: RXNO
id: RXNO:0000034

Axiom
annotated source: Mitsunobu reaction
annotated property: definition
annotated target: A substitution where an alcohol is converted into something else. Typical reagents are a dialkyl azodicarboxylate and a triarylphosphine. The alcohol stereocentre is inverted.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Stille coupling
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: organotin compound
definition: A carbon-carbon coupling reaction where a stannane reacts with an organohalide or organotriflate.
database_cross_reference: NAMERXN:3.4
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r415/
database_cross_reference: https://www.wikidata.org/wiki/Q899861
has_exact_synonym: Stille reaction
has_obo_namespace: RXNO
id: RXNO:0000035

Axiom
annotated source: Stille coupling
annotated property: definition
annotated target: A carbon-carbon coupling reaction where a stannane reacts with an organohalide or organotriflate.
database_cross_reference: RSC:db

Reformatsky reaction
type: Class
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has_part
  some values from: ketone reduction
subclass of: Restriction
  on property: has_part
  some values from: dehalogenation
definition: A carbon-carbon coupling reaction where an aldehyde or amine reacts with a alpha-halo ester and zinc to form a beta-hydroxy ester.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r361/
database_cross_reference: https://www.wikidata.org/wiki/Q898948
has_exact_synonym: Reformatskii reaction
has_obo_namespace: RXNO
id: RXNO:0000036

Axiom
annotated source: Reformatsky reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction where an aldehyde or amine reacts with a alpha-halo ester and zinc to form a beta-hydroxy ester.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

functional group reduction
type: Class
equivalent class: Class
  intersection of: functional group modification
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: functional reduction objective
subclass of: functional group modification
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: functional reduction objective
definition: A functional group modification reaction where a functional group is reduced.
has_obo_namespace: RXNO
id: RXNO:0000037

Axiom
annotated source: functional group reduction
annotated property: definition
annotated target: A functional group modification reaction where a functional group is reduced.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Clemmensen reduction
type: Class
subclass of: functional group reduction
definition: A functional group reduction where an aldehyde or ketone carbonyl group is reduced to a methylene with zinc-mercury amalgam and hydrochloric acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r82/
database_cross_reference: https://www.wikidata.org/wiki/Q898480
has_obo_namespace: RXNO
id: RXNO:0000038

Axiom
annotated source: Clemmensen reduction
annotated property: definition
annotated target: A functional group reduction where an aldehyde or ketone carbonyl group is reduced to a methylene with zinc-mercury amalgam and hydrochloric acid.
database_cross_reference: RSC:db

carbon-carbon homocoupling reaction
type: Class
subclass of: carbon-carbon coupling reaction
definition: A joining reaction where a carbon-carbon bond is formed between like moieties.
has_obo_namespace: RXNO
id: RXNO:0000039

Axiom
annotated source: carbon-carbon homocoupling reaction
annotated property: definition
annotated target: A joining reaction where a carbon-carbon bond is formed between like moieties.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Ullmann reaction
type: Class
subclass of: carbon-carbon homocoupling reaction
definition: A carbon-carbon homocoupling reaction of an aryl halide mediated by copper.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r441/
database_cross_reference: https://www.wikidata.org/wiki/Q904703
has_obo_namespace: RXNO
id: RXNO:0000040

Axiom
annotated source: Ullmann reaction
annotated property: definition
annotated target: A carbon-carbon homocoupling reaction of an aryl halide mediated by copper.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

addition reaction step
type: Class
equivalent class: Class
  intersection of: functional modification
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: addition objective
subclass of: functional group modification
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: addition objective
definition: A reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order.
has_obo_namespace: RXNO
id: RXNO:0000041

Axiom
annotated source: addition reaction step
annotated property: definition
annotated target: A reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Birch reduction
type: Class
subclass of: addition reaction step
definition: Addition of hydrogen atoms to aromatic rings by means of alkali metals in liquid ammonia.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r44/
database_cross_reference: https://www.wikidata.org/wiki/Q864996
has_obo_namespace: RXNO
id: RXNO:0000042

Axiom
annotated source: Birch reduction
annotated property: definition
annotated target: Addition of hydrogen atoms to aromatic rings by means of alkali metals in liquid ammonia.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Claisen condensation
type: Class
subclass of: deethanolative condensation
subclass of: molecular skeleton joining reaction
definition: A carbon-carbon coupling reaction of an ester and a carbonyl compound to form a beta-keto ester.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r79/
database_cross_reference: https://www.wikidata.org/wiki/Q898501
has_obo_namespace: RXNO
id: RXNO:0000043

Axiom
annotated source: Claisen condensation
annotated property: definition
annotated target: A carbon-carbon coupling reaction of an ester and a carbonyl compound to form a beta-keto ester.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Knoevenagel condensation
type: Class
subclass of: decarboxylative condensation
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: A carbon-carbon coupling reaction of an aldehyde and a methylene compound.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r230/
database_cross_reference: https://www.wikidata.org/wiki/Q898972
has_obo_namespace: RXNO
id: RXNO:0000044

Axiom
annotated source: Knoevenagel condensation
annotated property: definition
annotated target: A carbon-carbon coupling reaction of an aldehyde and a methylene compound.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Friedel-Crafts acylation
type: Class
subclass of: Friedel-Crafts reaction
subclass of: Restriction
  on property: has_part
  some values from: Lewis acid catalysis
definition: A carbon-carbon coupling reaction between an arene and a carbonyl compound (usually an acyl halide) to give an aryl ketone. The reaction is catalysed by a Lewis acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r158/
database_cross_reference: https://www.wikidata.org/wiki/Q15130933
has_obo_namespace: RXNO
id: RXNO:0000045

Axiom
annotated source: Friedel-Crafts acylation
annotated property: definition
annotated target: A carbon-carbon coupling reaction between an arene and a carbonyl compound (usually an acyl halide) to give an aryl ketone. The reaction is catalysed by a Lewis acid.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Friedel-Crafts alkylation
type: Class
subclass of: Friedel-Crafts reaction
subclass of: Restriction
  on property: has_part
  some values from: Lewis acid catalysis
definition: A carbon-carbon coupling reaction between an arene and an alkyl halide/alkene/alcohol (anything that can form a carbocation) to give a substituted arene. The reaction is catalysed by a Lewis acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r158/
has_obo_namespace: RXNO
id: RXNO:0000046
comment: It proceeds by an SN1 mechanism.

Axiom
annotated source: Friedel-Crafts alkylation
annotated property: definition
annotated target: A carbon-carbon coupling reaction between an arene and an alkyl halide/alkene/alcohol (anything that can form a carbocation) to give a substituted arene. The reaction is catalysed by a Lewis acid.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Oppenauer oxidation
type: Class
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: ketone
subclass of: Restriction
  on property: has specified reactant
  some values from: secondary alcohol
subclass of: Restriction
  on property: has_catalyst
  some values from: metal atom
definition: An oxidation of a secondary alcohol to a ketone involving an equilibrium between the alcohol and a reagent ketone present in excess, catalysed by a metal alkoxide.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r311/
database_cross_reference: https://www.wikidata.org/wiki/Q902263
has_obo_namespace: RXNO
id: RXNO:0000047

Axiom
annotated source: Oppenauer oxidation
annotated property: definition
annotated target: An oxidation of a secondary alcohol to a ketone involving an equilibrium between the alcohol and a reagent ketone present in excess, catalysed by a metal alkoxide.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Prins reaction
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: formaldehyde
subclass of: Restriction
  on property: has_part
  some values from: Brønsted acid catalysis
definition: A carbon-carbon coupling between formaldehyde and an alkene to give a 1,3-diol or an allylic alcohol, catalysed by acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r352/
database_cross_reference: https://www.wikidata.org/wiki/Q267374
has_obo_namespace: RXNO
id: RXNO:0000048
comment: See also "intramolecular Prins reaction".

Axiom
annotated source: Prins reaction
annotated property: definition
annotated target: A carbon-carbon coupling between formaldehyde and an alkene to give a 1,3-diol or an allylic alcohol, catalysed by acid.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

intramolecular Prins reaction
type: Class
subclass of: ring formation reaction step
subclass of: Restriction
  on property: has specified reactant
  some values from: formaldehyde
subclass of: Restriction
  on property: has_part
  some values from: Brønsted acid catalysis
definition: A reaction between formaldehyde and an alkene to give a 1,3-dioxane, catalysed by acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r352/
has_obo_namespace: RXNO
id: RXNO:0000049

Axiom
annotated source: intramolecular Prins reaction
annotated property: definition
annotated target: A reaction between formaldehyde and an alkene to give a 1,3-dioxane, catalysed by acid.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

pinacol rearrangement
type: Class
subclass of: rearrangement step
subclass of: Restriction
  on property: has_part
  some values from: Brønsted acid catalysis
definition: A rearrangement of a 1,2-diol to give a carbonyl compound, catalysed by acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r341/
database_cross_reference: https://www.wikidata.org/wiki/Q902209
has_obo_namespace: RXNO
id: RXNO:0000050

Axiom
annotated source: pinacol rearrangement
annotated property: definition
annotated target: A rearrangement of a 1,2-diol to give a carbonyl compound, catalysed by acid.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Wolff rearrangement
type: Class
subclass of: rearrangement step
definition: A rearrangement of a diazoketone to give a ketene, with the elimination of molecular nitrogen.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r474/
database_cross_reference: https://www.wikidata.org/wiki/Q255452
has_obo_namespace: RXNO
id: RXNO:0000051

Axiom
annotated source: Wolff rearrangement
annotated property: definition
annotated target: A rearrangement of a diazoketone to give a ketene, with the elimination of molecular nitrogen.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

fused-ring-system formation
type: Class
equivalent class: Class
  intersection of: molecular process
  intersection of: Restriction
    on property: has specified product
    some values from: fused compound
subclass of: ring formation reaction step
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: fused-ring-system formation objective
subclass of: Restriction
  on property: has specified product
  some values from: fused compound
definition: A reaction in which a fused ring system is present in a product that was not present in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000052

Axiom
annotated source: fused-ring-system formation
annotated property: definition
annotated target: A reaction in which a fused ring system is present in a product that was not present in any of the reactants.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Bischler-Napieralski reaction
type: Class
subclass of: fused-ring-system formation
definition: A cyclodehydration of a beta-phenethylamide to give a 3,4-dihydroisoquinoline.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r46/
database_cross_reference: https://www.wikidata.org/wiki/Q866098
has_exact_synonym: Bischler-Napieralski 3,4-dihydroisoquinoline synthesis
has_exact_synonym: Bischler-Napieralski dihydroisoquinoline synthesis
has_exact_synonym: Bischler-Napieralski isoquinoline synthesis
has_obo_namespace: RXNO
id: RXNO:0000053

Axiom
annotated source: Bischler-Napieralski reaction
annotated property: definition
annotated target: A cyclodehydration of a beta-phenethylamide to give a 3,4-dihydroisoquinoline.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Curtius rearrangement
type: Class
subclass of: rearrangement step
subclass of: Restriction
  on property: has specified product
  some values from: isocyanates
subclass of: Restriction
  on property: has specified reactant
  some values from: azide
definition: A rearrangement of an acyl azide to give an isocyanate by pyrolysis, with the elimination of molecular nitrogen.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r97/
database_cross_reference: https://www.wikidata.org/wiki/Q254370
has_exact_synonym: Curtius degradation
has_exact_synonym: Curtius reaction
has_obo_namespace: RXNO
id: RXNO:0000054

Axiom
annotated source: Curtius rearrangement
annotated property: definition
annotated target: A rearrangement of an acyl azide to give an isocyanate by pyrolysis, with the elimination of molecular nitrogen.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Vilsmeier-Haack reaction
type: Class
subclass of: formylation
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: formamides
subclass of: Restriction
  on property: has specified reactant
  some values from: arene
definition: A formylation of an activated arene with a disubstituted formamide to give an arenecarbaldehyde.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r444/
database_cross_reference: https://www.wikidata.org/wiki/Q903038
has_exact_synonym: Vilsmeier-Haack formylation
has_obo_namespace: RXNO
id: RXNO:0000055

Axiom
annotated source: Vilsmeier-Haack reaction
annotated property: definition
annotated target: A formylation of an activated arene with a disubstituted formamide to give an arenecarbaldehyde.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Horner-Wadsworth-Emmons reaction
type: Class
subclass of: olefination
subclass of: Restriction
  on property: has specified product
  some values from: olefin
subclass of: Restriction
  on property: has specified reactant
  some values from: carbonyl compound
subclass of: Restriction
  on property: has specified reactant
  some values from: organic phosphonate
definition: A carbon-carbon coupling reaction between a phosphonate and a carbonyl compound to give an olefin.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r468/
database_cross_reference: https://www.wikidata.org/wiki/Q905020
has_exact_synonym: Emmons reaction
has_exact_synonym: Horner-Emmons reaction
has_exact_synonym: Horner-Emmons-Wadsworth reaction
has_exact_synonym: Horner-Wadsworth-Emmons (HWE) olefination
has_exact_synonym: Horner-Wadsworth-Emmons olefination
has_exact_synonym: Horner-Wittig reaction
has_exact_synonym: Wadsworth-Emmons olefination
has_exact_synonym: Wadsworth-Emmons reaction
has_exact_synonym: Wadsworth-Emmons-Horner reaction
has_exact_synonym: Wittig-Horner reaction
has_obo_namespace: RXNO
id: RXNO:0000056

Axiom
annotated source: Horner-Wadsworth-Emmons reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction between a phosphonate and a carbonyl compound to give an olefin.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Horner reaction
type: Class
subclass of: olefination
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular skeleton joining objective
subclass of: Restriction
  on property: has specified product
  some values from: olefin
subclass of: Restriction
  on property: has specified reactant
  some values from: carbonyl compound
subclass of: Restriction
  on property: has specified reactant
  some values from: phosphine oxide
definition: A joining reaction between a phosphine oxide and a carbonyl compound to give an olefin.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r468/
has_obo_namespace: RXNO
id: RXNO:0000057

Axiom
annotated source: Horner reaction
annotated property: definition
annotated target: A joining reaction between a phosphine oxide and a carbonyl compound to give an olefin.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Ritter reaction
type: Class
subclass of: functional group modification
subclass of: Restriction
  on property: has_part
  some values from: Brønsted acid catalysis
definition: A reaction between an alcohol or alkene and a nitrile to give an amide, catalysed by a Bronsted acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r372/
database_cross_reference: https://www.wikidata.org/wiki/Q902273
has_obo_namespace: RXNO
id: RXNO:0000058
comment: Proceeds by an SN1 mechanism.

Axiom
annotated source: Ritter reaction
annotated property: definition
annotated target: A reaction between an alcohol or alkene and a nitrile to give an amide, catalysed by a Bronsted acid.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Pictet-Spengler reaction
type: Class
subclass of: condensation reaction
subclass of: fused-ring-system formation
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: A condensation-cyclisation of a beta-phenethylamine with an aldehyde to give a tetrahydroisoquinoline.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r338/
database_cross_reference: https://www.wikidata.org/wiki/Q899206
has_exact_synonym: Pictet-Spengler isoquinoline synthesis
has_exact_synonym: Pictet-Spengler tetrahydroisoquinoline synthesis
has_obo_namespace: RXNO
id: RXNO:0000059

Axiom
annotated source: Pictet-Spengler reaction
annotated property: definition
annotated target: A condensation-cyclisation of a beta-phenethylamine with an aldehyde to give a tetrahydroisoquinoline.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Arbuzov reaction
type: Class
subclass of: substitution step
subclass of: Restriction
  on property: has_part
  some values from: O-dealkylation
subclass of: Restriction
  on property: has_part
  some values from: P-alkylation
definition: The alkylation of a trialkyl phosphite with an alkyl halide or acyl halide to give an alkyl phosphonate.
has_alternative_id: RXNO:0000112
database_cross_reference: https://www.wikidata.org/wiki/Q630801
has_exact_synonym: Michaelis-Arbuzov phosphonate synthesis
has_exact_synonym: Michaelis-Arbuzov reaction
has_obo_namespace: RXNO
id: RXNO:0000060

Axiom
annotated source: Arbuzov reaction
annotated property: definition
annotated target: The alkylation of a trialkyl phosphite with an alkyl halide or acyl halide to give an alkyl phosphonate.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Mukaiyama aldol condensation
type: Class
subclass of: aldol condensation
definition: An aldol condensation between an aldehyde or ketone and a silyl enol ether (also known as a ketene silyl acetal) to give a beta-hydroxy carbonyl compound.
database_cross_reference: https://www.wikidata.org/wiki/Q1059787
has_exact_synonym: Mukaiyama aldol addition
has_exact_synonym: Mukaiyama aldol reaction
has_obo_namespace: RXNO
id: RXNO:0000061

Axiom
annotated source: Mukaiyama aldol condensation
annotated property: definition
annotated target: An aldol condensation between an aldehyde or ketone and a silyl enol ether (also known as a ketene silyl acetal) to give a beta-hydroxy carbonyl compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Skraup reaction
type: Class
subclass of: molecular dehydration reaction
subclass of: quinoline synthesis
subclass of: Restriction
  on property: has specified product
  some values from: quinolines
subclass of: Restriction
  on property: has specified reactant
  some values from: aromatic amine
definition: A condensation between an aromatic amine and glycerol to give a quinoline.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r403/
database_cross_reference: https://www.wikidata.org/wiki/Q903836
has_exact_synonym: Skraup quinoline synthesis
has_obo_namespace: RXNO
id: RXNO:0000062

Axiom
annotated source: Skraup reaction
annotated property: definition
annotated target: A condensation between an aromatic amine and glycerol to give a quinoline.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Arndt-Eistert reaction
type: Class
subclass of: molecular skeleton insertion reaction
subclass of: Restriction
  on property: has specified product
  some values from: carboxylic acid
subclass of: Restriction
  on property: has specified reactant
  some values from: carboxylic acid
subclass of: Restriction
  on property: has_intermediate
  some values from: acyl chloride
definition: A homologation reaction of a carboxylic acid to give the homologated carboxylic acid via acyl chloride and diazoketone intermediates.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r10/
database_cross_reference: https://www.wikidata.org/wiki/Q137617
has_exact_synonym: Arndt-Eistert synthesis
has_obo_namespace: RXNO
id: RXNO:0000063
comment: This is an insertion because the carbon atom is added between the R group and the carboxyl carbon in the starting material.

Axiom
annotated source: Arndt-Eistert reaction
annotated property: definition
annotated target: A homologation reaction of a carboxylic acid to give the homologated carboxylic acid via acyl chloride and diazoketone intermediates.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Fischer indole synthesis
type: Class
subclass of: indole synthesis
subclass of: Restriction
  on property: has specified reactant
  some values from: phenylhydrazine
definition: Reaction of an aldehyde or ketone with a phenylhydrazine to give an indole.
database_cross_reference: https://www.wikidata.org/wiki/Q901218
has_exact_synonym: Fischer indolisation
has_exact_synonym: Fischer indolization
has_obo_namespace: RXNO
id: RXNO:0000064

Axiom
annotated source: Fischer indole synthesis
annotated property: definition
annotated target: Reaction of an aldehyde or ketone with a phenylhydrazine to give an indole.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Dieckmann cyclisation
type: Class
subclass of: deethanolative condensation
subclass of: ring formation reaction step
definition: An intramolecular cyclisation of a diester to give a cyclic beta-ketoester.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r108/
database_cross_reference: https://www.wikidata.org/wiki/Q900932
has_exact_synonym: Dieckmann condensation
has_exact_synonym: Dieckmann cyclization
has_exact_synonym: Dieckmann reaction
has_obo_namespace: RXNO
id: RXNO:0000065
comment: This is the intramolecular version of the Claisen condensation.

Axiom
annotated source: Dieckmann cyclisation
annotated property: definition
annotated target: An intramolecular cyclisation of a diester to give a cyclic beta-ketoester.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Staudinger reaction
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: tertiary phosphine
definition: A joining of an organic azide and a tertiary phosphine to give a phosphazo compound.
database_cross_reference: https://www.wikidata.org/wiki/Q903726
has_exact_synonym: Staudinger ligation
has_exact_synonym: Staudinger reduction
has_obo_namespace: RXNO
id: RXNO:0000066
comment: Hydrolysis of the phosphazo compound gives the corresponding amine." [https://orcid.org/0000-0002-4077-4719, RSC:db]

Axiom
annotated source: Staudinger reaction
annotated property: definition
annotated target: A joining of an organic azide and a tertiary phosphine to give a phosphazo compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

benzidine rearrangement
type: Class
subclass of: extrusion reaction
definition: A rearrangement of a hydrazobenzene to give a diaminobiphenyl compound.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r33/
database_cross_reference: https://www.wikidata.org/wiki/Q465781
has_obo_namespace: RXNO
id: RXNO:0000067

Axiom
annotated source: benzidine rearrangement
annotated property: definition
annotated target: A rearrangement of a hydrazobenzene to give a diaminobiphenyl compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

semidine rearrangement
type: Class
subclass of: extrusion reaction
definition: A rearrangement of a p-substituted hydrazobenzene to give a p-aminodiphenylamine.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r33/
has_obo_namespace: RXNO
id: RXNO:0000068

Axiom
annotated source: semidine rearrangement
annotated property: definition
annotated target: A rearrangement of a p-substituted hydrazobenzene to give a p-aminodiphenylamine.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Dimroth rearrangement
type: Class
subclass of: ring rearrangement
definition: A rearrangement of a heterocyclic compound in which endocyclic and exocyclic heteroatoms swap places.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r111/
database_cross_reference: https://www.wikidata.org/wiki/Q902659
has_obo_namespace: RXNO
id: RXNO:0000069

Axiom
annotated source: Dimroth rearrangement
annotated property: definition
annotated target: A rearrangement of a heterocyclic compound in which endocyclic and exocyclic heteroatoms swap places.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

chain lengthening
type: Class
equivalent class: Class
  intersection of: molecular skeleton joining reaction
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: molecular chain lengthening objective
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular chain lengthening objective
definition: A molecular skeleton joining reaction in which a chain part of a molecular skeleton is lengthened.
has_obo_namespace: RXNO
id: RXNO:0000070

Axiom
annotated source: chain lengthening
annotated property: definition
annotated target: A molecular skeleton joining reaction in which a chain part of a molecular skeleton is lengthened.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Edman degradation
type: Class
subclass of: terminal amino-acid residue cleaving reaction
subclass of: Restriction
  on property: has specified product
  some values from: amine
subclass of: Restriction
  on property: has specified reactant
  some values from: peptide
definition: A cleaving reaction in which a peptide is treated with phenylisothiocyanate, removing the terminal amino acid group, to form the chain-shortened amine and a phenylthiohydantoin.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r122/
database_cross_reference: https://www.wikidata.org/wiki/Q898506
has_obo_namespace: RXNO
id: RXNO:0000071
comment: The latter can be used to identify the terminal amino acid, and the process repeated to enable peptide sequencing."

Axiom
annotated source: Edman degradation
annotated property: definition
annotated target: A cleaving reaction in which a peptide is treated with phenylisothiocyanate, removing the terminal amino acid group, to form the chain-shortened amine and a phenylthiohydantoin.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Reimer-Tiemann reaction
type: Class
subclass of: formylation
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has specified product
  some values from: phenols
subclass of: Restriction
  on property: has specified reactant
  some values from: chloroform
definition: A formylation reaction between a phenol and chloroform (for example, to form an ortho-formyl phenol).
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r362/
has_obo_namespace: RXNO
id: RXNO:0000072

Axiom
annotated source: Reimer-Tiemann reaction
annotated property: definition
annotated target: A formylation reaction between a phenol and chloroform (for example, to form an ortho-formyl phenol).
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

cleaving reaction
type: Class
equivalent class: Class
  intersection of: planned reaction step
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: molecular skeleton cleaving objective
subclass of: planned reaction step
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular skeleton cleaving objective
definition: A reaction where atoms are lost from the molecular skeleton.
has_obo_namespace: RXNO
id: RXNO:0000073

Axiom
annotated source: cleaving reaction
annotated property: definition
annotated target: A reaction where atoms are lost from the molecular skeleton.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Wurtz reaction
type: Class
subclass of: carbon-carbon homocoupling reaction
definition: A carbon-carbon homocoupling reaction of two molecules of an alkyl halide with sodium to give a symmetrical product.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r478/
database_cross_reference: https://www.wikidata.org/wiki/Q898901
has_exact_synonym: Wurtz coupling
has_obo_namespace: RXNO
id: RXNO:0000074

Axiom
annotated source: Wurtz reaction
annotated property: definition
annotated target: A carbon-carbon homocoupling reaction of two molecules of an alkyl halide with sodium to give a symmetrical product.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

benzilic acid rearrangement
type: Class
subclass of: rearrangement step
definition: A rearrangement of a 1,2-diketone to an alpha-hydroxy carboxylic acid. It can also be applied to alpha-keto aldehydes. The first exmaple of this reaction was with benzil (PhC(=O)C(=O)Ph) to form benzilic acid, hence the name.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r34/
database_cross_reference: https://www.wikidata.org/wiki/Q818488
has_obo_namespace: RXNO
id: RXNO:0000075

Axiom
annotated source: benzilic acid rearrangement
annotated property: definition
annotated target: A rearrangement of a 1,2-diketone to an alpha-hydroxy carboxylic acid. It can also be applied to alpha-keto aldehydes. The first exmaple of this reaction was with benzil (PhC(=O)C(=O)Ph) to form benzilic acid, hence the name.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Baylis-Hillman reaction
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: A carbon-carbon coupling of an aldehyde to an activated alkene in the presence of a nucleophilic base to give an alpha-hydroxyalkylated compound.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r27/
database_cross_reference: https://www.wikidata.org/wiki/Q812563
has_exact_synonym: MBH reaction
has_exact_synonym: Morita-Baylis-Hillman reaction
has_obo_namespace: RXNO
id: RXNO:0000076

Axiom
annotated source: Baylis-Hillman reaction
annotated property: definition
annotated target: A carbon-carbon coupling of an aldehyde to an activated alkene in the presence of a nucleophilic base to give an alpha-hydroxyalkylated compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Darzens reaction
type: Class
subclass of: decarboxylative condensation
subclass of: molecular skeleton joining reaction
definition: A coupling of an aldehyde or ketone with an alpha-halo ester to form an alpha,beta-epoxy ester, which hydrolyses to yield aldehydes or ketones by elimination of carbon dioxide.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r101/
database_cross_reference: https://www.wikidata.org/wiki/Q899351
has_exact_synonym: Darzens condensation
has_exact_synonym: Darzens-Claisen reaction
has_exact_synonym: glycidic ester condensation
has_obo_namespace: RXNO
id: RXNO:0000077

Axiom
annotated source: Darzens reaction
annotated property: definition
annotated target: A coupling of an aldehyde or ketone with an alpha-halo ester to form an alpha,beta-epoxy ester, which hydrolyses to yield aldehydes or ketones by elimination of carbon dioxide.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

protection reaction
type: Class
equivalent class: Class
  intersection of: functional modification
  intersection of: Restriction
    on property: protects
    some values from: group
subclass of: functional modification
subclass of: Restriction
  on property: protects
  some values from: group
subclass of: Restriction
  on property: part_of
  some values from: planned synthesis
disjoint with: deprotection reaction
definition: A reaction in which a functional group is modified by converting it into a protecting group, in order to make subsequent reactions more selective.
database_cross_reference: NAMERXN:5
has_obo_namespace: RXNO
id: RXNO:0000078

Axiom
annotated source: protection reaction
annotated property: definition
annotated target: A reaction in which a functional group is modified by converting it into a protecting group, in order to make subsequent reactions more selective.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Boc protection
type: Class
subclass of: amino group protection
subclass of: Restriction
  on property: protects
  some values from: amino group
subclass of: Restriction
  on property: has specified reactant
  some values from: amine
definition: A protection reaction in which an amine is converted into a tert-butoxycarbonyl compound.
has_obo_namespace: RXNO
id: RXNO:0000079

Axiom
annotated source: Boc protection
annotated property: definition
annotated target: A protection reaction in which an amine is converted into a tert-butoxycarbonyl compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Peterson olefination
type: Class
subclass of: olefination
subclass of: Restriction
  on property: has specified product
  some values from: olefin
definition: A carbon-carbon coupling reaction in which an alpha-silyl carbanion reacts with an aldehyde or a ketone to give an alkene, proceeding via a beta-hydroxysilane. The stereochemistry of the alkene can be controlled by treating the intermediate with acid or base.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r331/
database_cross_reference: https://www.wikidata.org/wiki/Q900350
has_exact_synonym: Peterson reaction
has_obo_namespace: RXNO
id: RXNO:0000080

Axiom
annotated source: Peterson olefination
annotated property: definition
annotated target: A carbon-carbon coupling reaction in which an alpha-silyl carbanion reacts with an aldehyde or a ketone to give an alkene, proceeding via a beta-hydroxysilane. The stereochemistry of the alkene can be controlled by treating the intermediate with acid or base.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Ullmann condensation
type: Class
subclass of: aromatic substitution step
definition: A coupling reaction in which a phenol is coupled to an aryl halide to give a diaryl ether in the presence of a copper compound.
database_cross_reference: https://www.wikidata.org/wiki/Q2371705
has_exact_synonym: Ullmann ether synthesis
has_obo_namespace: RXNO
id: RXNO:0000081

Axiom
annotated source: Ullmann condensation
annotated property: definition
annotated target: A coupling reaction in which a phenol is coupled to an aryl halide to give a diaryl ether in the presence of a copper compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Goldberg reaction
type: Class
subclass of: aromatic substitution step
definition: A coupling reaction in which an acetanilide is coupled to an aryl halide to give an N-acetyl diaryl amine in the presence of a copper compound.
has_obo_namespace: RXNO
id: RXNO:0000082

Axiom
annotated source: Goldberg reaction
annotated property: definition
annotated target: A coupling reaction in which an acetanilide is coupled to an aryl halide to give an N-acetyl diaryl amine in the presence of a copper compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Paternò–Büchi reaction
type: Class
subclass of: [2+2] cycloaddition
subclass of: oxacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: oxetanes
definition: A photochemical cycloaddition between an aldehyde or ketone and an alkene to give an oxetane.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r319/
database_cross_reference: https://www.wikidata.org/wiki/Q902254
has_exact_synonym: Paterno-Buchi reaction
has_obo_namespace: RXNO
id: RXNO:0000083

Axiom
annotated source: Paternò–Büchi reaction
annotated property: definition
annotated target: A photochemical cycloaddition between an aldehyde or ketone and an alkene to give an oxetane.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Barbier reaction
type: Class
equivalent class: Class
  union of: aldehyde Barbier reaction
  union of: ketone Barbier reaction
subclass of: molecular skeleton joining reaction
definition: A joining reaction between an aldehyde or ketone and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a secondary or tertiary alcohol.
database_cross_reference: https://www.wikidata.org/wiki/Q807848
has_obo_namespace: RXNO
id: RXNO:0000084

Axiom
annotated source: Barbier reaction
annotated property: definition
annotated target: A joining reaction between an aldehyde or ketone and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a secondary or tertiary alcohol.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

acyloin condensation
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: carboxylic ester
subclass of: Restriction
  on property: has_part
  some values from: condensation reaction
definition: A reductive coupling reaction between two esters to give an acyloin (an alpha-hydroxyketone).
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r2/
database_cross_reference: https://www.wikidata.org/wiki/Q345007
has_obo_namespace: RXNO
id: RXNO:0000085

Axiom
annotated source: acyloin condensation
annotated property: definition
annotated target: A reductive coupling reaction between two esters to give an acyloin (an alpha-hydroxyketone).
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Henry reaction
type: Class
subclass of: carbon-carbon coupling reaction
definition: A carbon-carbon coupling reaction between a nitroalkane and an aldehyde or ketone to give a beta-hydroxy nitroalkane.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r196/
database_cross_reference: https://www.wikidata.org/wiki/Q903747
has_exact_synonym: nitro-aldol reaction
has_exact_synonym: nitroaldol reaction
has_obo_namespace: RXNO
id: RXNO:0000086

Axiom
annotated source: Henry reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction between a nitroalkane and an aldehyde or ketone to give a beta-hydroxy nitroalkane.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Barton reaction
type: Class
subclass of: rearrangement step
subclass of: Restriction
  on property: has specified reactant
  some values from: nitrate ester
definition: The photolytic oxidation of a nitrate ester to give a gamma-nitroalcohol.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r24/
database_cross_reference: https://www.wikidata.org/wiki/Q809549
has_obo_namespace: RXNO
id: RXNO:0000087

Axiom
annotated source: Barton reaction
annotated property: definition
annotated target: The photolytic oxidation of a nitrate ester to give a gamma-nitroalcohol.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Negishi coupling
type: Class
subclass of: carbon-carbon coupling reaction
definition: A carbon-carbon coupling reaction between an organohalide or organotriflate and an organozinc compound. The reaction is catalysed by palladium or nickel.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r299/
database_cross_reference: https://www.wikidata.org/wiki/Q902756
has_exact_synonym: Negishi cross-coupling
has_obo_namespace: RXNO
id: RXNO:0000088

Axiom
annotated source: Negishi coupling
annotated property: definition
annotated target: A carbon-carbon coupling reaction between an organohalide or organotriflate and an organozinc compound. The reaction is catalysed by palladium or nickel.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Meerwein-Ponndorf-Verley reduction
type: Class
equivalent class: Class
  union of: Meerwein-Ponndorf-Verley reduction of an aldehyde
  union of: Meerwein-Ponndorf-Verley reduction of a ketone
subclass of: functional group reduction
subclass of: Restriction
  on property: has specified reactant
  some values from: alcohol
definition: A reduction of an aldehyde or ketone to an alcohol involving an equilibrium between the aldehyde or ketone and a reagent alcohol present in excess, catalysed by a metal alkoxide. This reaction is the reverse of the Oppenauer oxidation (RXNO:0000047).
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r272/
database_cross_reference: https://www.wikidata.org/wiki/Q903026
has_obo_namespace: RXNO
id: RXNO:0000089

Axiom
annotated source: Meerwein-Ponndorf-Verley reduction
annotated property: definition
annotated target: A reduction of an aldehyde or ketone to an alcohol involving an equilibrium between the aldehyde or ketone and a reagent alcohol present in excess, catalysed by a metal alkoxide. This reaction is the reverse of the Oppenauer oxidation (RXNO:0000047).
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Williamson ether synthesis
type: Class
subclass of: substitution step
definition: The reaction between an alkyl halide or alkyl sulfate and a metal alkoxide to give an ether.
database_cross_reference: https://www.wikidata.org/wiki/Q898790
has_exact_synonym: Williamson etherification
has_obo_namespace: RXNO
id: RXNO:0000090

Axiom
annotated source: Williamson ether synthesis
annotated property: definition
annotated target: The reaction between an alkyl halide or alkyl sulfate and a metal alkoxide to give an ether.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Wittig methylenation
type: Class
subclass of: Wittig reaction
definition: A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give a terminal alkene.
has_obo_namespace: RXNO
id: RXNO:0000091

Axiom
annotated source: Wittig methylenation
annotated property: definition
annotated target: A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give a terminal alkene.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

aza-Diels-Alder reaction
type: Class
subclass of: hetero-Diels-Alder reaction
definition: A Diels-Alder reaction between a diene and an imine or an azadiene and an alkene to give a six-membered nitrogen-containing ring compound.
database_cross_reference: https://www.wikidata.org/wiki/Q2042393
has_exact_synonym: aza Diels-Alder cycloaddition
has_exact_synonym: aza Diels-Alder reaction
has_exact_synonym: aza-Diels-Alder cycloaddition
has_exact_synonym: azo Diels-Alder cycloaddition
has_exact_synonym: azo Diels-Alder reaction
has_exact_synonym: azo-Diels-Alder cycloaddition
has_exact_synonym: azo-Diels-Alder reaction
has_obo_namespace: RXNO
id: RXNO:0000092

Axiom
annotated source: aza-Diels-Alder reaction
annotated property: definition
annotated target: A Diels-Alder reaction between a diene and an imine or an azadiene and an alkene to give a six-membered nitrogen-containing ring compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

extrusion reaction
type: Class
equivalent class: Class
  intersection of: cleaving reaction
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: molecular extrusion objective
subclass of: cleaving reaction
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular extrusion objective
definition: A cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule.
database_cross_reference: https://www.wikidata.org/wiki/Q31287730
has_obo_namespace: RXNO
id: RXNO:0000093

Axiom
annotated source: extrusion reaction
annotated property: definition
annotated target: A cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Ramberg-Bäcklund reaction
type: Class
subclass of: extrusion reaction
definition: The reaction of an alpha-halosulfone to give an alkene, with the extrusion of sulfur dioxide.
database_cross_reference: https://www.wikidata.org/wiki/Q1935557
has_exact_synonym: Ramberg-Backlund reaction
has_obo_namespace: RXNO
id: RXNO:0000094

Axiom
annotated source: Ramberg-Bäcklund reaction
annotated property: definition
annotated target: The reaction of an alpha-halosulfone to give an alkene, with the extrusion of sulfur dioxide.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Fischer-Hepp rearrangement
type: Class
subclass of: rearrangement step
definition: The rearrangement of an aromatic nitrosamine to a para-nitrosoaniline.
database_cross_reference: https://www.wikidata.org/wiki/Q1968891
has_obo_namespace: RXNO
id: RXNO:0000095

Axiom
annotated source: Fischer-Hepp rearrangement
annotated property: definition
annotated target: The rearrangement of an aromatic nitrosamine to a para-nitrosoaniline.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

azo coupling
type: Class
subclass of: functional group modification
definition: A coupling reaction of a diazonium salt with a phenol or aniline to give an azo compound.
database_cross_reference: https://www.wikidata.org/wiki/Q668665
has_obo_namespace: RXNO
id: RXNO:0000096

Axiom
annotated source: azo coupling
annotated property: definition
annotated target: A coupling reaction of a diazonium salt with a phenol or aniline to give an azo compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

imino-Reformatsky reaction
type: Class
subclass of: Reformatsky reaction
definition: A carbon-carbon coupling reaction where an imine reacts with a alpha-halo ester and zinc to form a beta-amino ester.
has_exact_synonym: imino Reformatsky reaction
has_obo_namespace: RXNO
id: RXNO:0000097

Axiom
annotated source: imino-Reformatsky reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction where an imine reacts with a alpha-halo ester and zinc to form a beta-amino ester.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Glaser coupling
type: Class
subclass of: molecular skeleton joining reaction
subclass of: carbon-carbon homocoupling reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: terminal acetylenic compound
definition: A coupling reaction between two molecules of a terminal alkyne catalysed by Cu(I) salts.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r169/
database_cross_reference: https://www.wikidata.org/wiki/Q514335
has_obo_namespace: RXNO
id: RXNO:0000098

Axiom
annotated source: Glaser coupling
annotated property: definition
annotated target: A coupling reaction between two molecules of a terminal alkyne catalysed by Cu(I) salts.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Eglinton reaction
type: Class
subclass of: molecular skeleton joining reaction
subclass of: carbon-carbon homocoupling reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: terminal acetylenic compound
definition: A coupling reaction between two molecules of a terminal alkyne using stoichiometric Cu(II) salts.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r169/
has_exact_synonym: Eglinton coupling
has_obo_namespace: RXNO
id: RXNO:0000099

Axiom
annotated source: Eglinton reaction
annotated property: definition
annotated target: A coupling reaction between two molecules of a terminal alkyne using stoichiometric Cu(II) salts.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Cadiot-Chodkiewicz coupling
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: terminal acetylenic compound
definition: A coupling reaction between a terminal alkyne and an alkynyl halide catalysed by Cu(I) salts.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r169/
database_cross_reference: https://www.wikidata.org/wiki/Q903015
has_obo_namespace: RXNO
id: RXNO:0000100

Axiom
annotated source: Cadiot-Chodkiewicz coupling
annotated property: definition
annotated target: A coupling reaction between a terminal alkyne and an alkynyl halide catalysed by Cu(I) salts.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Leuckart reaction
type: Class
equivalent class: Class
  union of: Leuckart aldehyde reaction
  union of: Leuckart ketone reaction
subclass of: reductive amination
definition: The reductive amination of ketones or aldehydes with an ammonium formate or formamide to form an amine.
database_cross_reference: https://www.wikidata.org/wiki/Q726513
has_obo_namespace: RXNO
id: RXNO:0000101

Axiom
annotated source: Leuckart reaction
annotated property: definition
annotated target: The reductive amination of ketones or aldehydes with an ammonium formate or formamide to form an amine.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Leuckart-Wallach reaction
type: Class
subclass of: reductive amination
definition: The reductive amination of ketones or aldehydes with an amine and formic acid to form amines.
database_cross_reference: https://www.wikidata.org/wiki/Q726513
has_exact_synonym: Wallach reaction
has_obo_namespace: RXNO
id: RXNO:0000102

Axiom
annotated source: Leuckart-Wallach reaction
annotated property: definition
annotated target: The reductive amination of ketones or aldehydes with an amine and formic acid to form amines.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Gabriel synthesis
type: Class
subclass of: substitution step
subclass of: Restriction
  on property: has_part
  some values from: hydrolysis
definition: The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by hydrolysis, to give the corresponding primary amine.
database_cross_reference: https://www.wikidata.org/wiki/Q123422
has_obo_namespace: RXNO
id: RXNO:0000103

Axiom
annotated source: Gabriel synthesis
annotated property: definition
annotated target: The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by hydrolysis, to give the corresponding primary amine.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Ing-Manske procedure
type: Class
subclass of: substitution step
definition: The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by treatment with hydrazine, to give the corresponding primary amine.
has_obo_namespace: RXNO
id: RXNO:0000104

Axiom
annotated source: Ing-Manske procedure
annotated property: definition
annotated target: The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by treatment with hydrazine, to give the corresponding primary amine.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

end-of-chain chain shortening
type: Class
equivalent class: Class
  intersection of: cleaving reaction
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: end-of-chain chain shortening objective
subclass of: cleaving reaction
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: end-of-chain chain shortening objective
definition: A reaction in which a single skeletal atom is removed from the end of a chain.
has_obo_namespace: RXNO
id: RXNO:0000105

Axiom
annotated source: end-of-chain chain shortening
annotated property: definition
annotated target: A reaction in which a single skeletal atom is removed from the end of a chain.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Hunsdiecker reaction
type: Class
subclass of: end-of-chain chain shortening
definition: The decarboxylation of silver carboxylates with halogens to give organic halides.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r215/
database_cross_reference: https://www.wikidata.org/wiki/Q902216
has_exact_synonym: Borodin reaction
has_exact_synonym: Borodine reaction
has_obo_namespace: RXNO
id: RXNO:0000106

Axiom
annotated source: Hunsdiecker reaction
annotated property: definition
annotated target: The decarboxylation of silver carboxylates with halogens to give organic halides.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

malonic ester synthesis
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular skeleton joining objective
subclass of: Restriction
  on property: has specified product
  some values from: carboxylic acid
subclass of: Restriction
  on property: has specified reactant
  some values from: haloalkane
definition: A carbon-carbon coupling reaction between a dialkyl malonate and an alkyl halide, to give a substituted acetic acid. The base/R'X treatment can be repeated to give a disubstituted product.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r264/
database_cross_reference: https://www.wikidata.org/wiki/Q902284
has_obo_namespace: RXNO
id: RXNO:0000107

Axiom
annotated source: malonic ester synthesis
annotated property: definition
annotated target: A carbon-carbon coupling reaction between a dialkyl malonate and an alkyl halide, to give a substituted acetic acid. The base/R'X treatment can be repeated to give a disubstituted product.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

ring expansion
type: Class
subclass of: ring formation reaction step
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular ring expansion objective
definition: A reaction in which an existing ring is increased in size.
has_exact_synonym: ring enlargement
has_obo_namespace: RXNO
id: RXNO:0000108

Axiom
annotated source: ring expansion
annotated property: definition
annotated target: A reaction in which an existing ring is increased in size.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Pfitzinger reaction
type: Class
subclass of: ring expansion
definition: The reaction between isatin and an alpha-methylene carbonyl compound to give a substituted quinoline-4-carboxylic acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r334/
database_cross_reference: https://www.wikidata.org/wiki/Q1580484
has_exact_synonym: Pfitzinger quinoline synthesis
has_exact_synonym: Pfitzinger-Borsche reaction
has_obo_namespace: RXNO
id: RXNO:0000109

Axiom
annotated source: Pfitzinger reaction
annotated property: definition
annotated target: The reaction between isatin and an alpha-methylene carbonyl compound to give a substituted quinoline-4-carboxylic acid.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

fragmentation reaction
type: Class
equivalent class: Class
  intersection of: cleaving reaction
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: molecular fragmentation objective
subclass of: cleaving reaction
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular fragmentation objective
definition: A reaction in which the parent molecule breaks up into three or more products.
has_obo_namespace: RXNO
id: RXNO:0000110

Axiom
annotated source: fragmentation reaction
annotated property: definition
annotated target: A reaction in which the parent molecule breaks up into three or more products.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Grob fragmentation
type: Class
subclass of: fragmentation reaction
definition: The fragmentation of a molecule that takes place when an electron-donating fragment (X) and an electron-accepting fragment (X') are situated at positions 1 and 3 on an aliphatic chain, to give a cationic fragment, a neutral fragment (e.g. an alkene) and an anionic fragment.
database_cross_reference: https://www.wikidata.org/wiki/Q5609896
has_obo_namespace: RXNO
id: RXNO:0000111

Axiom
annotated source: Grob fragmentation
annotated property: definition
annotated target: The fragmentation of a molecule that takes place when an electron-donating fragment (X) and an electron-accepting fragment (X') are situated at positions 1 and 3 on an aliphatic chain, to give a cationic fragment, a neutral fragment (e.g. an alkene) and an anionic fragment.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

RXNO_0000112
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: Arbuzov reaction
deprecated: true

Brook rearrangement
type: Class
subclass of: rearrangement step
definition: The rearrangement of an alpha-, beta- or gamma-hydroxy silane to give a silyl ether. It is catalysed by a base.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r62/
database_cross_reference: https://www.wikidata.org/wiki/Q2558021
has_obo_namespace: RXNO
id: RXNO:0000113

Axiom
annotated source: Brook rearrangement
annotated property: definition
annotated target: The rearrangement of an alpha-, beta- or gamma-hydroxy silane to give a silyl ether. It is catalysed by a base.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Nicholas reaction
type: Class
equivalent class: Class
  union of: Nicholas reaction, nucleophilic heteroatom centre
  union of: Nicholas reaction, nucleophilic carbon centre
subclass of: substitution step
definition: The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophile to give a substituted alkyne.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r303/
database_cross_reference: https://www.wikidata.org/wiki/Q902932
has_obo_namespace: RXNO
id: RXNO:0000114

Axiom
annotated source: Nicholas reaction
annotated property: definition
annotated target: The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophile to give a substituted alkyne.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Nicholas reaction, nucleophilic heteroatom centre
type: Class
subclass of: Nicholas reaction
definition: The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a hydride or amine or enamine to give a substituted alkyne.
has_obo_namespace: RXNO
id: RXNO:0000115

Axiom
annotated source: Nicholas reaction, nucleophilic heteroatom centre
annotated property: definition
annotated target: The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a hydride or amine or enamine to give a substituted alkyne.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Nicholas reaction, nucleophilic carbon centre
type: Class
subclass of: carbon-carbon coupling reaction
subclass of: Nicholas reaction
definition: The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophilic carbon centre (on e.g. enolates, allyl silanes, ketones, electron-rich aromatics, beta-dicarbonyl compounds) to give a substituted alkyne.
has_obo_namespace: RXNO
id: RXNO:0000116

Axiom
annotated source: Nicholas reaction, nucleophilic carbon centre
annotated property: definition
annotated target: The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophilic carbon centre (on e.g. enolates, allyl silanes, ketones, electron-rich aromatics, beta-dicarbonyl compounds) to give a substituted alkyne.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Julia olefination
type: Class
subclass of: olefination
subclass of: Restriction
  on property: has specified product
  some values from: olefin
definition: A carbon-carbon coupling reaction between a phenyl sulfone and an aldehyde or ketone to give a (typically trans) alkene.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r224/
database_cross_reference: https://www.wikidata.org/wiki/Q902237
has_exact_synonym: Julia-Lythgoe olefination
has_obo_namespace: RXNO
id: RXNO:0000117

Axiom
annotated source: Julia olefination
annotated property: definition
annotated target: A carbon-carbon coupling reaction between a phenyl sulfone and an aldehyde or ketone to give a (typically trans) alkene.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Sommelet reaction
type: Class
subclass of: functional group modification
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
definition: The oxidation of a benzylic halide to give an aldehyde. The reaction uses hexamethylenetetramine.
database_cross_reference: https://www.wikidata.org/wiki/Q909040
has_obo_namespace: RXNO
id: RXNO:0000118

Axiom
annotated source: Sommelet reaction
annotated property: definition
annotated target: The oxidation of a benzylic halide to give an aldehyde. The reaction uses hexamethylenetetramine.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Bouveault-Blanc reaction
type: Class
subclass of: functional group reduction
subclass of: Restriction
  on property: has specified product
  some values from: alcohol
subclass of: Restriction
  on property: has specified reactant
  some values from: sodium atom
subclass of: Restriction
  on property: has specified reactant
  some values from: carboxylic ester
definition: The reduction of an ester using sodium to give two alcohols.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r58/
database_cross_reference: https://www.wikidata.org/wiki/Q895315
has_exact_synonym: Bouveault-Blanc procedure
has_exact_synonym: Bouveault-Blanc reduction
has_obo_namespace: RXNO
id: RXNO:0000119

Axiom
annotated source: Bouveault-Blanc reaction
annotated property: definition
annotated target: The reduction of an ester using sodium to give two alcohols.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Payne rearrangement
type: Class
subclass of: ring rearrangement
definition: A base-catalysed isomerisation of a 2,3-epoxyalcohol, with inversion of configuration at C2.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r321/
database_cross_reference: https://www.wikidata.org/wiki/Q983127
has_obo_namespace: RXNO
id: RXNO:0000120

Axiom
annotated source: Payne rearrangement
annotated property: definition
annotated target: A base-catalysed isomerisation of a 2,3-epoxyalcohol, with inversion of configuration at C2.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

aza-Payne rearrangement
type: Class
subclass of: ring rearrangement
definition: A base-catalysed isomerisation of a 2,3-epoxyamine to form a hydroxy aziridine, with inversion of configuration at C2.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r321/
has_obo_namespace: RXNO
id: RXNO:0000121

Axiom
annotated source: aza-Payne rearrangement
annotated property: definition
annotated target: A base-catalysed isomerisation of a 2,3-epoxyamine to form a hydroxy aziridine, with inversion of configuration at C2.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Baker-Venkataraman rearrangement
type: Class
subclass of: rearrangement step
definition: The base-catalysed rearrangement of an o-acetoxyacetophenone to give a hydroxyphenyl-1,3-diketone.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r14/
database_cross_reference: https://www.wikidata.org/wiki/Q804325
has_obo_namespace: RXNO
id: RXNO:0000122

Axiom
annotated source: Baker-Venkataraman rearrangement
annotated property: definition
annotated target: The base-catalysed rearrangement of an o-acetoxyacetophenone to give a hydroxyphenyl-1,3-diketone.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

molecular skeleton elimination reaction
type: Class
equivalent class: Class
  intersection of: functional modification
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: molecular skeleton elimination objective
subclass of: functional modification
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular skeleton elimination objective
definition: A reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order.
has_obo_namespace: RXNO
id: RXNO:0000123
comment: This is narrower in focus than elimination in general in that we're focussing on the aims of the chemist.

Axiom
annotated source: molecular skeleton elimination reaction
annotated property: definition
annotated target: A reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Bamford-Stevens reaction
type: Class
subclass of: molecular skeleton elimination reaction
subclass of: Restriction
  on property: has specified product
  some values from: olefin
definition: The reaction of a tosylhydrazone of an aldehyde or ketone with a strong base to give an olefin.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r16/
database_cross_reference: https://www.wikidata.org/wiki/Q575939
has_obo_namespace: RXNO
id: RXNO:0000124
comment: This generally provides the more-substituted olefin as the thermodynamic product.

Axiom
annotated source: Bamford-Stevens reaction
annotated property: definition
annotated target: The reaction of a tosylhydrazone of an aldehyde or ketone with a strong base to give an olefin.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Shapiro reaction
type: Class
subclass of: molecular skeleton elimination reaction
subclass of: Restriction
  on property: has specified product
  some values from: olefin
subclass of: Restriction
  on property: has specified reactant
  some values from: organomagnesium halide
subclass of: Restriction
  on property: has specified reactant
  some values from: alkyllithium compound
definition: The reaction of a tosylhydrazone of an aldehyde or ketone with an alkyllithium or Grignard reagent to give an olefin.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r16/
database_cross_reference: https://www.wikidata.org/wiki/Q846597
has_obo_namespace: RXNO
id: RXNO:0000125
comment: This generally provides the less-substituted olefin as the kinetic product.

Axiom
annotated source: Shapiro reaction
annotated property: definition
annotated target: The reaction of a tosylhydrazone of an aldehyde or ketone with an alkyllithium or Grignard reagent to give an olefin.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Doebner reaction
type: Class
subclass of: quinoline synthesis
subclass of: Restriction
  on property: has specified product
  some values from: quinolines
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: pyruvic acid
subclass of: Restriction
  on property: has specified reactant
  some values from: aromatic amine
definition: The reaction between an aromatic amine, an aldehyde and pyruvic acid on heating to give a quinoline 4-carboxylic acid (cinchoninic acid).
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r114/
database_cross_reference: https://www.wikidata.org/wiki/Q3772250
has_obo_namespace: RXNO
id: RXNO:0000126

Axiom
annotated source: Doebner reaction
annotated property: definition
annotated target: The reaction between an aromatic amine, an aldehyde and pyruvic acid on heating to give a quinoline 4-carboxylic acid (cinchoninic acid).
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Balz-Schiemann reaction
type: Class
subclass of: aromatic substitution step
subclass of: Restriction
  on property: has specified product
  some values from: fluoroarene
subclass of: Restriction
  on property: has specified reactant
  some values from: aromatic amine
definition: The conversion of an aromatic amine to the corresponding fluoride via the diazonium fluoroborate.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r388/
database_cross_reference: https://www.wikidata.org/wiki/Q572113
has_exact_synonym: Schiemann reaction
has_obo_namespace: RXNO
id: RXNO:0000127

Axiom
annotated source: Balz-Schiemann reaction
annotated property: definition
annotated target: The conversion of an aromatic amine to the corresponding fluoride via the diazonium fluoroborate.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Kolbe electrolysis
type: Class
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: aromatic amine
definition: The decarboxylation and coupling of a carboxylate or mixture of carboxylates to give a dimer.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r238/
database_cross_reference: https://www.wikidata.org/wiki/Q901771
has_exact_synonym: Crum-Brown-Walker reaction
has_exact_synonym: Kolbe electrolytic synthesis
has_exact_synonym: Kolbe electrosynthesis
has_exact_synonym: Kolbe reaction
has_obo_namespace: RXNO
id: RXNO:0000128

Axiom
annotated source: Kolbe electrolysis
annotated property: definition
annotated target: The decarboxylation and coupling of a carboxylate or mixture of carboxylates to give a dimer.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Ugi reaction
type: Class
subclass of: molecular dehydration reaction
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: primary amine
subclass of: Restriction
  on property: has specified reactant
  some values from: carboxylic acid
definition: Reaction of a ketone or aldehyde, amine, an isocyanide and carboxylic acid to form a bisamide.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r440/
database_cross_reference: https://www.wikidata.org/wiki/Q2002373
has_exact_synonym: 4CC
has_exact_synonym: Ugi four-component condensation
has_exact_synonym: Ugi-4CR
has_obo_namespace: RXNO
id: RXNO:0000129

Axiom
annotated source: Ugi reaction
annotated property: definition
annotated target: Reaction of a ketone or aldehyde, amine, an isocyanide and carboxylic acid to form a bisamide.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Wacker-Tsuji oxidation
type: Class
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified reactant
  some values from: dioxygen
subclass of: Restriction
  on property: has_catalyst
  some values from: copper(II) chloride
subclass of: Restriction
  on property: has_catalyst
  some values from: palladium(II) chloride
definition: The oxidation of a terminal alkene or ethene to a methyl ketone or acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r452/
has_exact_synonym: Wacker oxidation
has_exact_synonym: Wacker reaction
has_obo_namespace: RXNO
id: RXNO:0000130

Axiom
annotated source: Wacker-Tsuji oxidation
annotated property: definition
annotated target: The oxidation of a terminal alkene or ethene to a methyl ketone or acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Wacker process
type: Class
subclass of: Wacker-Tsuji oxidation
definition: The oxidation of ethene to acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant.
database_cross_reference: https://www.wikidata.org/wiki/Q578923
has_obo_namespace: RXNO
id: RXNO:0000131

Axiom
annotated source: Wacker process
annotated property: definition
annotated target: The oxidation of ethene to acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Monsanto process
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: carbon monoxide
definition: The reaction of carbon monoxide with methanol to form acetic acid, catalysed by a rhodium complex.
database_cross_reference: https://www.wikidata.org/wiki/Q901246
has_obo_namespace: RXNO
id: RXNO:0000132

Axiom
annotated source: Monsanto process
annotated property: definition
annotated target: The reaction of carbon monoxide with methanol to form acetic acid, catalysed by a rhodium complex.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Cativa process
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: carbon monoxide
definition: The reaction of carbon monoxide with methanol to form acetic acid, catalysed by an iridium complex.
database_cross_reference: https://www.wikidata.org/wiki/Q579304
has_obo_namespace: RXNO
id: RXNO:0000133

Axiom
annotated source: Cativa process
annotated property: definition
annotated target: The reaction of carbon monoxide with methanol to form acetic acid, catalysed by an iridium complex.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Barton-McCombie deoxygenation
type: Class
subclass of: functional group reduction
definition: The deoxygenation of an alcohol to the corresponding alkane using a thiochloroformate. It proceeds by a radical mechanism.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r22/
database_cross_reference: https://www.wikidata.org/wiki/Q809548
has_exact_synonym: Barton deoxygenation
has_exact_synonym: Barton reduction
has_obo_namespace: RXNO
id: RXNO:0000134

Axiom
annotated source: Barton-McCombie deoxygenation
annotated property: definition
annotated target: The deoxygenation of an alcohol to the corresponding alkane using a thiochloroformate. It proceeds by a radical mechanism.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Barton decarboxylation
type: Class
subclass of: end-of-chain chain shortening
definition: The decarboxylation of a carboxylic acid to the lower homologue alkane using a pyridine thione.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r21/
database_cross_reference: https://www.wikidata.org/wiki/Q3454335
has_obo_namespace: RXNO
id: RXNO:0000135
comment: The reaction proceeds by a radical mechanism.

Axiom
annotated source: Barton decarboxylation
annotated property: definition
annotated target: The decarboxylation of a carboxylic acid to the lower homologue alkane using a pyridine thione.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Rosenmund reduction
type: Class
subclass of: functional group reduction
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: acyl halide
subclass of: Restriction
  on property: has_catalyst
  some values from: palladium atom
definition: The hydrogenolysis of an acyl halide to the corresponding aldehyde, catalysed by palladium-on-barium sulfate.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r375/
database_cross_reference: https://www.wikidata.org/wiki/Q905524
has_exact_synonym: Rosenmund reaction
has_obo_namespace: RXNO
id: RXNO:0000136

Axiom
annotated source: Rosenmund reduction
annotated property: definition
annotated target: The hydrogenolysis of an acyl halide to the corresponding aldehyde, catalysed by palladium-on-barium sulfate.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

Sonogashira coupling
type: Class
subclass of: molecular skeleton joining reaction
subclass of: palladium-catalysed carbon-carbon coupling reaction
subclass of: Restriction
  on property: has specified product
  some values from: terminal acetylenic compound
subclass of: Restriction
  on property: has_catalyst
  some values from: palladium atom
definition: A carbon-carbon coupling reaction where a terminal alkyne reacts with an aryl halide to give an aryl alkyne. It is catalysed by palladium.
database_cross_reference: NAMERXN:3.3
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r408/
database_cross_reference: https://www.wikidata.org/wiki/Q900334
has_exact_synonym: Hagihara-Sonogashira coupling
has_exact_synonym: Sonogashira cross-coupling
has_exact_synonym: Sonogashira reaction
has_obo_namespace: RXNO
id: RXNO:0000137

Axiom
annotated source: Sonogashira coupling
annotated property: definition
annotated target: A carbon-carbon coupling reaction where a terminal alkyne reacts with an aryl halide to give an aryl alkyne. It is catalysed by palladium.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

benzoin condensation
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: A reaction between two aromatic aldehydes to give a benzoin (an alpha-hydroxyketone).
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r35/
database_cross_reference: https://www.wikidata.org/wiki/Q818514
has_exact_synonym: benzoin addition
has_obo_namespace: RXNO
id: RXNO:0000138

Axiom
annotated source: benzoin condensation
annotated property: definition
annotated target: A reaction between two aromatic aldehydes to give a benzoin (an alpha-hydroxyketone).
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Gattermann reaction
type: Class
subclass of: formylation
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: arene
subclass of: Restriction
  on property: has_part
  some values from: Lewis acid catalysis
definition: The formylation of an arene with hydrogen cyanide to give an aryl aldehyde or ketone.
has_obo_namespace: RXNO
id: RXNO:0000139
comment: This is essentially a variant of the Friedel-Crafts acylation.

Axiom
annotated source: Gattermann reaction
annotated property: definition
annotated target: The formylation of an arene with hydrogen cyanide to give an aryl aldehyde or ketone.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Suzuki-Miyaura coupling
type: Class
subclass of: Suzuki-type coupling
subclass of: Restriction
  on property: has_catalyst
  some values from: platinum atom
definition: The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate catalysed by a palladium(0) complex.
database_cross_reference: NAMERXN:3.1
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r424/
database_cross_reference: https://www.wikidata.org/wiki/Q899891
has_exact_synonym: Suzuki coupling reaction
has_exact_synonym: Suzuki cross-coupling
has_exact_synonym: Suzuki cross-coupling reaction
has_exact_synonym: Suzuki reaction
has_exact_synonym: Suzuki-Miyaura coupling
has_exact_synonym: Suzuki-Miyaura coupling reaction
has_exact_synonym: Suzuki-Miyaura cross-coupling
has_exact_synonym: Suzuki-Miyaura cross-coupling reaction
has_exact_synonym: Suzuki-Miyaura reaction
has_obo_namespace: RXNO
id: RXNO:0000140

Axiom
annotated source: Suzuki-Miyaura coupling
annotated property: definition
annotated target: The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate catalysed by a palladium(0) complex.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Sharpless asymmetric epoxidation
type: Class
subclass of: epoxidation
subclass of: oxacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: epoxide
subclass of: Restriction
  on property: has_catalyst
  some values from: titanium atom
definition: The epoxidation of an allylic alcohol to give a beta,gamma-epoxy alcohol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is tert-butyl hydroperoxide, and the catalyst is a complex of titanium salt and optically active diethyl tartrate.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r397/
database_cross_reference: https://www.wikidata.org/wiki/Q56672072
has_exact_synonym: Katsuki-Sharpless asymmetric epoxidation
has_exact_synonym: Katsuki-Sharpless epoxidation
has_exact_synonym: Sharpless epoxidation
has_exact_synonym: Sharpless-Katsuki asymmetric epoxidation
has_exact_synonym: Sharpless-Katsuki epoxidation
has_obo_namespace: RXNO
id: RXNO:0000141

Axiom
annotated source: Sharpless asymmetric epoxidation
annotated property: definition
annotated target: The epoxidation of an allylic alcohol to give a beta,gamma-epoxy alcohol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is tert-butyl hydroperoxide, and the catalyst is a complex of titanium salt and optically active diethyl tartrate.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Sharpless asymmetric dihydroxylation
type: Class
subclass of: addition reaction step
definition: The dihydroxylation of an alkene to give an alpha,beta-diol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is osmium tetroxide, which is used catalytically with a stoichiometric oxidant and a chiral ligand. The reagents are available commercially as AD-mix.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r396/
database_cross_reference: https://www.wikidata.org/wiki/Q752651
has_exact_synonym: Sharpless bishydroxylation
has_exact_synonym: Sharpless hydroxylation
has_obo_namespace: RXNO
id: RXNO:0000142

Axiom
annotated source: Sharpless asymmetric dihydroxylation
annotated property: definition
annotated target: The dihydroxylation of an alkene to give an alpha,beta-diol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is osmium tetroxide, which is used catalytically with a stoichiometric oxidant and a chiral ligand. The reagents are available commercially as AD-mix.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Sharpless asymmetric aminohydroxylation
type: Class
subclass of: addition reaction step
definition: The aminohydroxylation of an alkene to give a beta-amino alcohol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is an oxygen-containing osmium species and/or an amino derivative which can be used catalytically with a stoichiometric oxidant and a chiral ligand.
has_exact_synonym: Sharpless oxyamination
has_obo_namespace: RXNO
id: RXNO:0000143

Axiom
annotated source: Sharpless asymmetric aminohydroxylation
annotated property: definition
annotated target: The aminohydroxylation of an alkene to give a beta-amino alcohol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is an oxygen-containing osmium species and/or an amino derivative which can be used catalytically with a stoichiometric oxidant and a chiral ligand.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Kumada coupling
type: Class
equivalent class: Class
  union of: palladium-catalysed Kumada coupling
  union of: nickel-catalysed Kumada coupling
subclass of: carbon-carbon coupling reaction
definition: A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a palladium or nickel catalyst.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r248/
database_cross_reference: https://www.wikidata.org/wiki/Q899278
has_exact_synonym: Kharasch cross-coupling
has_exact_synonym: Kumada cross-coupling
has_obo_namespace: RXNO
id: RXNO:0000144

Axiom
annotated source: Kumada coupling
annotated property: definition
annotated target: A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a palladium or nickel catalyst.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Barbier-Wieland degradation
type: Class
subclass of: end-of-chain chain shortening
definition: The degradation of a carboxylic acid to its next lower homologous carboxylic acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r18/
database_cross_reference: https://www.wikidata.org/wiki/Q5801440
has_exact_synonym: Barbier-Wieland procedure
has_obo_namespace: RXNO
id: RXNO:0000145

Axiom
annotated source: Barbier-Wieland degradation
annotated property: definition
annotated target: The degradation of a carboxylic acid to its next lower homologous carboxylic acid.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Corey-Fuchs reaction
type: Class
subclass of: chain lengthening
subclass of: Restriction
  on property: has specified product
  some values from: terminal acetylenic compound
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: tetrabromomethane
subclass of: Restriction
  on property: has specified reactant
  some values from: butyllithium
subclass of: Restriction
  on property: has_part
  some values from: Fritsch-Buttenberg-Wiechell rearrangement
subclass of: Restriction
  on property: has_part
  some values from: Corey-Fuchs terminal dibromoolefination
definition: A homologation reaction of an aldehyde to yield a terminal alkyne. The reagents are tetrabromomethane, triphenylphosphine, butyllithium and water.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r89/
database_cross_reference: https://www.wikidata.org/wiki/Q903573
has_exact_synonym: Ramirez-Corey-Fuchs reaction
has_obo_namespace: RXNO
id: RXNO:0000146

Axiom
annotated source: Corey-Fuchs reaction
annotated property: definition
annotated target: A homologation reaction of an aldehyde to yield a terminal alkyne. The reagents are tetrabromomethane, triphenylphosphine, butyllithium and water.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Emde degradation
type: Class
subclass of: cleaving reaction
definition: A reduction of a quaternary ammonium salt containing at least one unsaturated substituent, to give a tertiary amine.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r127/
database_cross_reference: https://www.wikidata.org/wiki/Q2026108
has_exact_synonym: Emde reaction
has_exact_synonym: Emde reduction
has_obo_namespace: RXNO
id: RXNO:0000147

Axiom
annotated source: Emde degradation
annotated property: definition
annotated target: A reduction of a quaternary ammonium salt containing at least one unsaturated substituent, to give a tertiary amine.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Claisen rearrangement
type: Class
subclass of: [3,3]-sigmatropic rearrangement
subclass of: rearrangement step
definition: The [3,3]-sigmatropic rearrangement of an allyl vinyl ether to give a gamma,delta-unsaturated carbonyl compound.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r80/
database_cross_reference: https://www.wikidata.org/wiki/Q900936
has_obo_namespace: RXNO
id: RXNO:0000148

Axiom
annotated source: Claisen rearrangement
annotated property: definition
annotated target: The [3,3]-sigmatropic rearrangement of an allyl vinyl ether to give a gamma,delta-unsaturated carbonyl compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Ireland-Claisen rearrangement
type: Class
subclass of: [3,3]-sigmatropic rearrangement
subclass of: rearrangement step
definition: The enolisation and subsequent [3,3]-sigmatropic rearrangement of an allylic acetate to give a gamma,delta-unsaturated carboxylic acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r80/
database_cross_reference: https://www.wikidata.org/wiki/Q1945726
has_obo_namespace: RXNO
id: RXNO:0000149

Axiom
annotated source: Ireland-Claisen rearrangement
annotated property: definition
annotated target: The enolisation and subsequent [3,3]-sigmatropic rearrangement of an allylic acetate to give a gamma,delta-unsaturated carboxylic acid.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

joining with rearrangement
type: Class
equivalent class: Class
  intersection of: molecular skeleton joining reaction
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: joining with rearrangement objective
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: joining with rearrangement objective
definition: A reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs.
has_obo_namespace: RXNO
id: RXNO:0000150

Axiom
annotated source: joining with rearrangement
annotated property: definition
annotated target: A reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Bellus-Claisen rearrangement
type: Class
subclass of: [3,3]-sigmatropic rearrangement
subclass of: joining with rearrangement
definition: The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic ether or allylic thioether or allylic amine and a ketene to give the corresponding gamma,delta-unsaturated carbonyl compound.
has_obo_namespace: RXNO
id: RXNO:0000151

Axiom
annotated source: Bellus-Claisen rearrangement
annotated property: definition
annotated target: The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic ether or allylic thioether or allylic amine and a ketene to give the corresponding gamma,delta-unsaturated carbonyl compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Eschenmoser-Claisen rearrangement
type: Class
subclass of: [3,3]-sigmatropic rearrangement
subclass of: joining with rearrangement
definition: The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and alpha,alpha-dialkoxy ethylamine to give a gamma,delta-unsaturated dialkyl amide.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r80/
has_obo_namespace: RXNO
id: RXNO:0000152

Axiom
annotated source: Eschenmoser-Claisen rearrangement
annotated property: definition
annotated target: The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and alpha,alpha-dialkoxy ethylamine to give a gamma,delta-unsaturated dialkyl amide.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Johnson-Claisen rearrangement
type: Class
subclass of: [3,3]-sigmatropic rearrangement
subclass of: joining with rearrangement
definition: The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and trimethyl orthoacetate to give a gamma,delta-unsaturated alkyl ester.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r80/
has_obo_namespace: RXNO
id: RXNO:0000153

Axiom
annotated source: Johnson-Claisen rearrangement
annotated property: definition
annotated target: The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and trimethyl orthoacetate to give a gamma,delta-unsaturated alkyl ester.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Swern oxidation
type: Class
subclass of: alcohol oxidation
subclass of: functional group oxidation
definition: The oxidation of a primary alcohol or secondary alcohol to an aldehyde or ketone respectively. Does not work with allylic or benzylic alcohols.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r426
has_obo_namespace: RXNO
id: RXNO:0000154

Axiom
annotated source: Swern oxidation
annotated property: definition
annotated target: The oxidation of a primary alcohol or secondary alcohol to an aldehyde or ketone respectively. Does not work with allylic or benzylic alcohols.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Finkelstein reaction
type: Class
subclass of: functional group modification
definition: The conversion of an alkyl chloride, alkyl bromide or alkyl sulfonate ester to an alkyl iodide by SN2 substitution. The reaction relies upon the equilibrium being pushed to completion by the precipitation.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r141/
has_obo_namespace: RXNO
id: RXNO:0000155

Axiom
annotated source: Finkelstein reaction
annotated property: definition
annotated target: The conversion of an alkyl chloride, alkyl bromide or alkyl sulfonate ester to an alkyl iodide by SN2 substitution. The reaction relies upon the equilibrium being pushed to completion by the precipitation.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Lossen rearrangement
type: Class
subclass of: rearrangement step
definition: The derivatisation (for example with tosyl chloride) and subsequent rearrangement of a hydroxamic acid to give an isocyanate.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r259/
has_obo_namespace: RXNO
id: RXNO:0000156

Axiom
annotated source: Lossen rearrangement
annotated property: definition
annotated target: The derivatisation (for example with tosyl chloride) and subsequent rearrangement of a hydroxamic acid to give an isocyanate.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Nef reaction
type: Class
subclass of: functional group modification
definition: The conversion of a primary nitroalkane or secondary nitroalkane to an aldehyde or ketone, respectively.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r297/
has_obo_namespace: RXNO
id: RXNO:0000157

Axiom
annotated source: Nef reaction
annotated property: definition
annotated target: The conversion of a primary nitroalkane or secondary nitroalkane to an aldehyde or ketone, respectively.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Japp-Klingemann reaction
type: Class
subclass of: cleaving reaction
definition: The reaction of a doubly activated methylene compound that has at least one carbonyl substituent with an aryl azide to give a hydrazone. Usually there is concomitant cleaving and oxidation of one of the carbonyl substituents.
has_obo_namespace: RXNO
id: RXNO:0000158

Axiom
annotated source: Japp-Klingemann reaction
annotated property: definition
annotated target: The reaction of a doubly activated methylene compound that has at least one carbonyl substituent with an aryl azide to give a hydrazone. Usually there is concomitant cleaving and oxidation of one of the carbonyl substituents.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Doebner-Miller reaction
type: Class
subclass of: fused-ring-system formation
subclass of: Restriction
  on property: has specified reactant
  some values from: aromatic amine
definition: The formation of a quinoline from a primary aromatic amine and an alpha,beta-unsaturated carbonyl compound.
has_exact_synonym: Doebner-von Miller reaction
has_exact_synonym: Skraup-Doebner-von Miller quinoline synthesis
has_obo_namespace: RXNO
id: RXNO:0000159

Axiom
annotated source: Doebner-Miller reaction
annotated property: definition
annotated target: The formation of a quinoline from a primary aromatic amine and an alpha,beta-unsaturated carbonyl compound.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Fmoc protection
type: Class
subclass of: amino group protection
subclass of: Restriction
  on property: protects
  some values from: amino group
definition: The protection of an amine (often a peptide) as its 9H-fluoren-9-ylmethoxycarbonyl derivative.
has_obo_namespace: RXNO
id: RXNO:0000160

Axiom
annotated source: Fmoc protection
annotated property: definition
annotated target: The protection of an amine (often a peptide) as its 9H-fluoren-9-ylmethoxycarbonyl derivative.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Paal-Knorr synthesis
type: Class
subclass of: ring formation reaction step
definition: The cyclisation of a 1,4-dicarbonyl compound with another molecule to give a five-membered aromatic ring compound.
has_obo_namespace: RXNO
id: RXNO:0000161
comment: Usually this gives rise to a heterocycle.

Axiom
annotated source: Paal-Knorr synthesis
annotated property: definition
annotated target: The cyclisation of a 1,4-dicarbonyl compound with another molecule to give a five-membered aromatic ring compound.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Paal-Knorr furan synthesis
type: Class
subclass of: Paal-Knorr synthesis
subclass of: oxacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: furans
definition: The cyclisation of a 1,4-dicarbonyl compound with an acid catalyst to give a furan.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r315/
has_obo_namespace: RXNO
id: RXNO:0000162

Axiom
annotated source: Paal-Knorr furan synthesis
annotated property: definition
annotated target: The cyclisation of a 1,4-dicarbonyl compound with an acid catalyst to give a furan.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Paal-Knorr thiophene synthesis
type: Class
subclass of: Paal-Knorr synthesis
subclass of: thiacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: thiophenes
definition: The cyclisation of a 1,4-dicarbonyl compound with phosphorus pentasulfide to give a thiophene.
has_obo_namespace: RXNO
id: RXNO:0000163

Axiom
annotated source: Paal-Knorr thiophene synthesis
annotated property: definition
annotated target: The cyclisation of a 1,4-dicarbonyl compound with phosphorus pentasulfide to give a thiophene.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Paal-Knorr pyrrole synthesis
type: Class
subclass of: Paal-Knorr synthesis
subclass of: pyrrole synthesis
subclass of: Restriction
  on property: has specified product
  some values from: pyrroles
definition: The cyclisation of a 1,4-dicarbonyl compound with an amine to give a pyrrole.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r316/
has_obo_namespace: RXNO
id: RXNO:0000164
comment: Merck Index says "ammonia or primary amines"

Axiom
annotated source: Paal-Knorr pyrrole synthesis
annotated property: definition
annotated target: The cyclisation of a 1,4-dicarbonyl compound with an amine to give a pyrrole.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Schotten-Baumann reaction
type: Class
subclass of: substitution step
definition: The coupling of an alcohol or amine with an acyl chloride to give an ester or amide. A two-phase solvent system is often used, to enable the acid generated during the reaction to be neutralised by the aqueous base, while the starting materials and products remain in the organic phase.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r392/
has_obo_namespace: RXNO
id: RXNO:0000165

Axiom
annotated source: Schotten-Baumann reaction
annotated property: definition
annotated target: The coupling of an alcohol or amine with an acyl chloride to give an ester or amide. A two-phase solvent system is often used, to enable the acid generated during the reaction to be neutralised by the aqueous base, while the starting materials and products remain in the organic phase.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Hofmann elimination
type: Class
subclass of: molecular skeleton elimination reaction
subclass of: Restriction
  on property: has specified product
  some values from: olefin
subclass of: Restriction
  on property: has specified reactant
  some values from: alkylamine
definition: The elimination of a methylated amine from an alkylamine to form an olefin. The reaction proceeds via the quaternary ammonium salt.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r205/
has_exact_synonym: exhaustive methylation
has_obo_namespace: RXNO
has_related_synonym: Hofmann degradation
id: RXNO:0000166

Axiom
annotated source: Hofmann elimination
annotated property: definition
annotated target: The elimination of a methylated amine from an alkylamine to form an olefin. The reaction proceeds via the quaternary ammonium salt.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Fischer-Speier esterification
type: Class
subclass of: substitution step
definition: The esterification of a carboxylic acid with an alcohol. Various Lewis acids or Bronsted acids may be used as catalyst.
has_exact_synonym: Fischer esterification
has_obo_namespace: RXNO
id: RXNO:0000167

Axiom
annotated source: Fischer-Speier esterification
annotated property: definition
annotated target: The esterification of a carboxylic acid with an alcohol. Various Lewis acids or Bronsted acids may be used as catalyst.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Weerman reaction
type: Class
subclass of: end-of-chain chain shortening
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
definition: The degradation of an alpha-hydroxy amide or an alpha,beta-unsaturated amide to the lower homologue aldehyde, especially in carbohydrate chemistry. The process proceeds via Hofmann degradation.
has_exact_synonym: Weerman degradation
has_exact_synonym: Weerman's reaction
has_obo_namespace: RXNO
id: RXNO:0000168

Axiom
annotated source: Weerman reaction
annotated property: definition
annotated target: The degradation of an alpha-hydroxy amide or an alpha,beta-unsaturated amide to the lower homologue aldehyde, especially in carbohydrate chemistry. The process proceeds via Hofmann degradation.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Dakin reaction
type: Class
subclass of: cleaving reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: hydrogen peroxide
definition: The reaction of ortho- or para-phenolic (or ortho- or para-anilinic) aldehydes or ketones with hydrogen peroxide to form bisphenols (or hydroxy anilines) and carboxylic acids.
has_obo_namespace: RXNO
id: RXNO:0000169

Axiom
annotated source: Dakin reaction
annotated property: definition
annotated target: The reaction of ortho- or para-phenolic (or ortho- or para-anilinic) aldehydes or ketones with hydrogen peroxide to form bisphenols (or hydroxy anilines) and carboxylic acids.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Schmidt rearrangement, carboxylic acid
type: Class
subclass of: end-of-chain chain shortening
definition: The reaction of a carboxylic acid with hydrazoic acid to give the lower homologue amine, with the loss of the terminal carbon atom.
has_obo_namespace: RXNO
id: RXNO:0000170

Axiom
annotated source: Schmidt rearrangement, carboxylic acid
annotated property: definition
annotated target: The reaction of a carboxylic acid with hydrazoic acid to give the lower homologue amine, with the loss of the terminal carbon atom.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Schmidt rearrangement, ketone
type: Class
subclass of: molecular skeleton insertion reaction
definition: The reaction of a ketone with hydrazoic acid with the insertion of an NH group between the carbonyl carbon and one of the R groups to form an amide.
has_obo_namespace: RXNO
id: RXNO:0000171

Axiom
annotated source: Schmidt rearrangement, ketone
annotated property: definition
annotated target: The reaction of a ketone with hydrazoic acid with the insertion of an NH group between the carbonyl carbon and one of the R groups to form an amide.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Schmidt rearrangement, tertiary alcohol
type: Class
subclass of: molecular skeleton insertion reaction
definition: The reaction of a tertiary alcohol with hydrazoic acid with rearrangement to form an imide.
has_obo_namespace: RXNO
id: RXNO:0000172

Axiom
annotated source: Schmidt rearrangement, tertiary alcohol
annotated property: definition
annotated target: The reaction of a tertiary alcohol with hydrazoic acid with rearrangement to form an imide.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Schmidt rearrangement, alkene
type: Class
subclass of: molecular skeleton insertion reaction
definition: The reaction of an alkene with hydrazoic acid with rearrangement to form an imide.
has_obo_namespace: RXNO
id: RXNO:0000173

Axiom
annotated source: Schmidt rearrangement, alkene
annotated property: definition
annotated target: The reaction of an alkene with hydrazoic acid with rearrangement to form an imide.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Sommelet-Hauser rearrangement
type: Class
subclass of: rearrangement step
definition: The [2,3]-sigmatropic rearrangement of a benzyl quaternary ammonium salt to form an aniline.
has_obo_namespace: RXNO
id: RXNO:0000174

Axiom
annotated source: Sommelet-Hauser rearrangement
annotated property: definition
annotated target: The [2,3]-sigmatropic rearrangement of a benzyl quaternary ammonium salt to form an aniline.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Dakin-West reaction
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: acid anhydride
definition: The reaction of an amino acid with an acid anhydride to give an alpha-acylamido ketone. The reaction proceeds via the mixed anhydride and an oxazolone; the product is always racemic.
has_obo_namespace: RXNO
id: RXNO:0000175

Axiom
annotated source: Dakin-West reaction
annotated property: definition
annotated target: The reaction of an amino acid with an acid anhydride to give an alpha-acylamido ketone. The reaction proceeds via the mixed anhydride and an oxazolone; the product is always racemic.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Beckmann fragmentation
type: Class
subclass of: cleaving reaction
definition: The cleavage of an oxime to the corresponding nitrile and an alkyl halide. This reaction is related to the Beckmann rearrangement, and occurs when the R group that is anti to the oxime hydroxyl is quaternary.
has_obo_namespace: RXNO
id: RXNO:0000176

Axiom
annotated source: Beckmann fragmentation
annotated property: definition
annotated target: The cleavage of an oxime to the corresponding nitrile and an alkyl halide. This reaction is related to the Beckmann rearrangement, and occurs when the R group that is anti to the oxime hydroxyl is quaternary.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Kharasch reaction
type: Class
subclass of: chain lengthening
definition: The transfer of a hydrogen or halogen atom from a haloalkane to an alkene, giving the chain-extended halogenated alkane.
has_exact_synonym: Kharasch addition reaction
has_obo_namespace: RXNO
id: RXNO:0000177

Axiom
annotated source: Kharasch reaction
annotated property: definition
annotated target: The transfer of a hydrogen or halogen atom from a haloalkane to an alkene, giving the chain-extended halogenated alkane.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Kharasch-Sosnovsky reaction
type: Class
subclass of: substitution step
definition: The allylic oxidation of an alkene with a peroxy ester or a peroxide to give the corresponding allylic alcohol derivative. The catalyst is a copper compound.
has_obo_namespace: RXNO
id: RXNO:0000178

Axiom
annotated source: Kharasch-Sosnovsky reaction
annotated property: definition
annotated target: The allylic oxidation of an alkene with a peroxy ester or a peroxide to give the corresponding allylic alcohol derivative. The catalyst is a copper compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Elbs persulfate oxidation, phenol variant
type: Class
subclass of: aromatic substitution step
definition: The oxidation of a phenol to give a (predominantly para) diphenol using potassium persulfate.
has_obo_namespace: RXNO
id: RXNO:0000179

Axiom
annotated source: Elbs persulfate oxidation, phenol variant
annotated property: definition
annotated target: The oxidation of a phenol to give a (predominantly para) diphenol using potassium persulfate.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Elbs persulfate oxidation, tolyl variant
type: Class
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified product
  some values from: benzaldehydes
definition: The oxidation of a methyl-substituted aromatic compound to the corresponding benzaldehyde using potassium persulfate.
has_obo_namespace: RXNO
id: RXNO:0000180

Axiom
annotated source: Elbs persulfate oxidation, tolyl variant
annotated property: definition
annotated target: The oxidation of a methyl-substituted aromatic compound to the corresponding benzaldehyde using potassium persulfate.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Boyland-Sims oxidation
type: Class
subclass of: aromatic substitution step
subclass of: Restriction
  on property: has specified reactant
  some values from: aromatic amine
subclass of: Restriction
  on property: has_part
  some values from: hydrolysis
definition: The oxidation of an aromatic amine to give a (predominantly ortho) amino aryl sulfate using potassium persulfate followed by hydrolysis to yield the corresponding aminophenol.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r59/
has_obo_namespace: RXNO
id: RXNO:0000181

Axiom
annotated source: Boyland-Sims oxidation
annotated property: definition
annotated target: The oxidation of an aromatic amine to give a (predominantly ortho) amino aryl sulfate using potassium persulfate followed by hydrolysis to yield the corresponding aminophenol.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Kolbe-Schmitt reaction
type: Class
subclass of: carboxylation
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has participant ceasing to exist
  some values from: carbon dioxide
definition: The (predominantly ortho) carboxylation of a phenoxide.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r239/
has_obo_namespace: RXNO
id: RXNO:0000182

Axiom
annotated source: Kolbe-Schmitt reaction
annotated property: definition
annotated target: The (predominantly ortho) carboxylation of a phenoxide.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Perkow reaction
type: Class
subclass of: molecular skeleton joining reaction
definition: The reaction between an alpha-halocarbonyl compound and a trialkyl phosphite to give an enol phosphate.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r329/
has_obo_namespace: RXNO
id: RXNO:0000183
comment: not clear why this is where it is and not a sibling of the Arbuzov reaction (2014-02-17)

Axiom
annotated source: Perkow reaction
annotated property: definition
annotated target: The reaction between an alpha-halocarbonyl compound and a trialkyl phosphite to give an enol phosphate.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Pfitzner-Moffatt oxidation
type: Class
subclass of: functional group oxidation
definition: The oxidation of a primary or secondary alcohol to the corresponding aldehyde or ketone respectively using dimethyl sulfoxide, 1,3-dicyclohexylcarbodiimide and acid. The reaction proceeds via an alkoxysulfonium ylide.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r335/
has_exact_synonym: Moffatt oxidation
has_obo_namespace: RXNO
id: RXNO:0000184

Axiom
annotated source: Pfitzner-Moffatt oxidation
annotated property: definition
annotated target: The oxidation of a primary or secondary alcohol to the corresponding aldehyde or ketone respectively using dimethyl sulfoxide, 1,3-dicyclohexylcarbodiimide and acid. The reaction proceeds via an alkoxysulfonium ylide.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Willgerodt reaction
type: Class
subclass of: functional group modification
definition: The conversion of an aryl alkyl ketone to an amide and/or an ammonium salt of a carboxylic acid using ammonium polysulfide. The carbonyl group of the product is always at the end of the alkyl chain.
has_obo_namespace: RXNO
id: RXNO:0000185

Axiom
annotated source: Willgerodt reaction
annotated property: definition
annotated target: The conversion of an aryl alkyl ketone to an amide and/or an ammonium salt of a carboxylic acid using ammonium polysulfide. The carbonyl group of the product is always at the end of the alkyl chain.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Willgerodt-Kindler reaction
type: Class
subclass of: functional group modification
definition: The conversion of an aryl alkyl ketone to an amide using sulfur and dry ammonia or a primary or secondary amine. The amide carbonyl group is always at the end of the alkyl chain.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r466/
has_obo_namespace: RXNO
id: RXNO:0000186

Axiom
annotated source: Willgerodt-Kindler reaction
annotated property: definition
annotated target: The conversion of an aryl alkyl ketone to an amide using sulfur and dry ammonia or a primary or secondary amine. The amide carbonyl group is always at the end of the alkyl chain.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Tishchenko reaction
type: Class
subclass of: functional group modification
subclass of: Restriction
  on property: has specified product
  some values from: carboxylic ester
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: The formation of an ester from two aldehydes via a disproportionation process using a metal alkoxide to oxidise one aldehyde and reduce the other.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r433/
has_obo_namespace: RXNO
id: RXNO:0000187

Axiom
annotated source: Tishchenko reaction
annotated property: definition
annotated target: The formation of an ester from two aldehydes via a disproportionation process using a metal alkoxide to oxidise one aldehyde and reduce the other.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Zimmermann reaction
type: Class
subclass of: carbon-carbon coupling reaction
definition: The reaction between a methylene ketone and a polynitro aromatic compound.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r482/
has_obo_namespace: RXNO
id: RXNO:0000188

Axiom
annotated source: Zimmermann reaction
annotated property: definition
annotated target: The reaction between a methylene ketone and a polynitro aromatic compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Neber rearrangement
type: Class
subclass of: rearrangement step
definition: The rearrangement of the sulfonic ester of a ketoxime in base to give an alpha-amino ketone.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r296/
has_obo_namespace: RXNO
id: RXNO:0000189

Axiom
annotated source: Neber rearrangement
annotated property: definition
annotated target: The rearrangement of the sulfonic ester of a ketoxime in base to give an alpha-amino ketone.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

RXNO_0000190
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: Baeyer-Villiger oxidation
deprecated: true

Nozaki-Hiyama-Kishi reaction
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: A coupling reaction of an aldehyde to an allyl, vinyl or aryl halide or triflate in the presence of chromium(II). It is catalysed by nickel.
has_exact_synonym: Nozaki reaction
has_exact_synonym: Nozaki-Hiyama-Kishi coupling
has_exact_synonym: Nozaki-Kishi reaction
has_obo_namespace: RXNO
id: RXNO:0000191

Axiom
annotated source: Nozaki-Hiyama-Kishi reaction
annotated property: definition
annotated target: A coupling reaction of an aldehyde to an allyl, vinyl or aryl halide or triflate in the presence of chromium(II). It is catalysed by nickel.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Buchwald-Hartwig amination
type: Class
subclass of: aromatic substitution step
subclass of: Restriction
  on property: has_catalyst
  some values from: palladium atom
definition: A reaction in which an aryl halide or aryl triflate reacts with a primary or secondary amine in the presence of base to give a secondary or tertiary amine. It is catalysed by a palladium catalyst.
has_exact_synonym: Buchwald-Hartwig reaction
has_obo_namespace: RXNO
id: RXNO:0000192

Axiom
annotated source: Buchwald-Hartwig amination
annotated property: definition
annotated target: A reaction in which an aryl halide or aryl triflate reacts with a primary or secondary amine in the presence of base to give a secondary or tertiary amine. It is catalysed by a palladium catalyst.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Hiyama coupling
type: Class
subclass of: carbon-carbon coupling reaction
definition: A carbon-carbon coupling reaction where an organosilane reacts with an organic halide or triflate. It is catalysed by a palladium or nickel complex.
has_exact_synonym: Hiyama cross-coupling
has_obo_namespace: RXNO
id: RXNO:0000193

Axiom
annotated source: Hiyama coupling
annotated property: definition
annotated target: A carbon-carbon coupling reaction where an organosilane reacts with an organic halide or triflate. It is catalysed by a palladium or nickel complex.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Stevens rearrangement
type: Class
subclass of: rearrangement step
definition: The 1,2-rearrangement of an alpha-methylene ammonium salt or alpha-methylene sulfonium salt to an amine or sulfide in the presence of strong base.
has_obo_namespace: RXNO
id: RXNO:0000194

Axiom
annotated source: Stevens rearrangement
annotated property: definition
annotated target: The 1,2-rearrangement of an alpha-methylene ammonium salt or alpha-methylene sulfonium salt to an amine or sulfide in the presence of strong base.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Stevens rearrangement, ammonium
type: Class
subclass of: Stevens rearrangement
definition: The 1,2-rearrangement of an alpha-methylene ammonium salt to an amine in the presence of strong base.
has_obo_namespace: RXNO
id: RXNO:0000195

Axiom
annotated source: Stevens rearrangement, ammonium
annotated property: definition
annotated target: The 1,2-rearrangement of an alpha-methylene ammonium salt to an amine in the presence of strong base.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Stevens rearrangement, sulfonium
type: Class
subclass of: Stevens rearrangement
definition: The 1,2-rearrangement of an alpha-methylene sulfonium salt to a sulfide in the presence of strong base.
has_obo_namespace: RXNO
id: RXNO:0000196

Axiom
annotated source: Stevens rearrangement, sulfonium
annotated property: definition
annotated target: The 1,2-rearrangement of an alpha-methylene sulfonium salt to a sulfide in the presence of strong base.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

aza-Cope rearrangement
type: Class
subclass of: [3,3]-sigmatropic rearrangement
subclass of: rearrangement step
definition: A [3,3]-sigmatropic rearrangement where an aza-1,5-hexadiene rearranges to form an aza-1,5-hexadiene.
has_obo_namespace: RXNO
id: RXNO:0000197

Axiom
annotated source: aza-Cope rearrangement
annotated property: definition
annotated target: A [3,3]-sigmatropic rearrangement where an aza-1,5-hexadiene rearranges to form an aza-1,5-hexadiene.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

2-aza-Cope rearrangement
type: Class
subclass of: aza-Cope rearrangement
definition: The rearrangement of a 2-aza-1,5-hexadiene to form an imine.
has_obo_namespace: RXNO
id: RXNO:0000198

Axiom
annotated source: 2-aza-Cope rearrangement
annotated property: definition
annotated target: The rearrangement of a 2-aza-1,5-hexadiene to form an imine.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

3-aza-Cope rearrangement
type: Class
subclass of: aza-Cope rearrangement
definition: The rearrangement of a 3-aza-1,5-hexadiene to form a delta,epsilon-unsaturated imine.
has_exact_synonym: amino-Claisen rearrangement
has_exact_synonym: aza-Claisen rearrangement
has_obo_namespace: RXNO
id: RXNO:0000199
comment: This is the reverse of the 1-aza-Cope rearrangement.

Axiom
annotated source: 3-aza-Cope rearrangement
annotated property: definition
annotated target: The rearrangement of a 3-aza-1,5-hexadiene to form a delta,epsilon-unsaturated imine.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

1-aza-Cope rearrangement
type: Class
subclass of: aza-Cope rearrangement
definition: The rearrangement of a delta,epsilon-unsaturated imine to form a 3-aza-1,5-hexadiene.
has_obo_namespace: RXNO
id: RXNO:0000200
comment: This is the reverse of the 3-aza-Cope rearrangement.

Axiom
annotated source: 1-aza-Cope rearrangement
annotated property: definition
annotated target: The rearrangement of a delta,epsilon-unsaturated imine to form a 3-aza-1,5-hexadiene.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Steglich rearrangement
type: Class
subclass of: rearrangement step
definition: The rearrangement of an oxazolyl carbonate to a C-carboxyazlactone.
has_obo_namespace: RXNO
id: RXNO:0000201

Axiom
annotated source: Steglich rearrangement
annotated property: definition
annotated target: The rearrangement of an oxazolyl carbonate to a C-carboxyazlactone.
database_cross_reference: RSC:jrw
database_cross_reference: https://orcid.org/0000-0001-5985-7429

ring rearrangement
type: Class
equivalent class: Class
  intersection of: ring formation reaction step
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: molecular ring rearrangement objective
subclass of: ring formation reaction step
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular ring rearrangement objective
definition: A reaction in which the number of rings in a molecule stays the same but the connectivity of the atoms in at least one ring changes.
has_obo_namespace: RXNO
id: RXNO:0000202

Axiom
annotated source: ring rearrangement
annotated property: definition
annotated target: A reaction in which the number of rings in a molecule stays the same but the connectivity of the atoms in at least one ring changes.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

deprotection reaction
type: Class
equivalent class: Class
  intersection of: functional modification
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: deprotection objective
  intersection of: Restriction
    on property: deprotects
    some values from: group
subclass of: functional modification
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: deprotection objective
subclass of: Restriction
  on property: deprotects
  some values from: group
subclass of: Restriction
  on property: part_of
  some values from: planned synthesis
definition: A reaction in which a protecting group is modified by converting it into a functional group.
database_cross_reference: NAMERXN:6
has_obo_namespace: RXNO
id: RXNO:0000203

Axiom
annotated source: deprotection reaction
annotated property: definition
annotated target: A reaction in which a protecting group is modified by converting it into a functional group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

multiple-bond metathesis
type: Class
subclass of: molecular skeleton joining reaction
definition: A joining reaction in which two carbon-carbon multiple bonds are redistributed among two fragments. The reaction is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene.
has_exact_synonym: metathesis
has_exact_synonym: multiple bond metathesis
has_obo_namespace: RXNO
id: RXNO:0000204

Axiom
annotated source: multiple-bond metathesis
annotated property: definition
annotated target: A joining reaction in which two carbon-carbon multiple bonds are redistributed among two fragments. The reaction is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

ring breaking
type: Class
equivalent class: Class
  intersection of: planned reaction step
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: molecular ring breaking objective
subclass of: planned reaction step
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular ring breaking objective
definition: A planned reaction step in which the product has fewer rings than the reactants.
has_exact_synonym: ring opening
has_exact_synonym: selective ring opening
has_obo_namespace: RXNO
id: RXNO:0000205

Axiom
annotated source: ring breaking
annotated property: definition
annotated target: A planned reaction step in which the product has fewer rings than the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

ring contraction
type: Class
subclass of: ring formation reaction step
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular ring contraction objective
definition: A planned reaction step in which an existing ring is reduced in size.
has_obo_namespace: RXNO
id: RXNO:0000206

Axiom
annotated source: ring contraction
annotated property: definition
annotated target: A planned reaction step in which an existing ring is reduced in size.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Strecker reaction
type: Class
subclass of: chain lengthening
subclass of: Restriction
  on property: has_part
  some values from: hydrolysis
definition: An addition reaction between a carbonyl compound, an inorganic cyanide and an ammonium salt, followed by hydrolysis, to give an alpha-amino carboxylic acid.
has_obo_namespace: RXNO
id: RXNO:0000207

Axiom
annotated source: Strecker reaction
annotated property: definition
annotated target: An addition reaction between a carbonyl compound, an inorganic cyanide and an ammonium salt, followed by hydrolysis, to give an alpha-amino carboxylic acid.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

aromatic Claisen rearrangement
type: Class
subclass of: [3,3]-sigmatropic rearrangement
subclass of: rearrangement step
definition: The [3,3]-sigmatropic rearrangement, and subsequent re-aromatisation, of an allyl aryl ether to give an ortho-allyl phenol.
has_obo_namespace: RXNO
id: RXNO:0000208

Axiom
annotated source: aromatic Claisen rearrangement
annotated property: definition
annotated target: The [3,3]-sigmatropic rearrangement, and subsequent re-aromatisation, of an allyl aryl ether to give an ortho-allyl phenol.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Nazarov cyclisation
type: Class
subclass of: ring formation reaction step
subclass of: Restriction
  on property: has_part
  some values from: acid catalysis
definition: The acid-catalysed cyclisation of a divinylketone to give a cyclopentenone.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r295/
has_exact_synonym: Nazarov cyclization
has_obo_namespace: RXNO
id: RXNO:0000209

Axiom
annotated source: Nazarov cyclisation
annotated property: definition
annotated target: The acid-catalysed cyclisation of a divinylketone to give a cyclopentenone.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Fleming-Tamao oxidation
type: Class
subclass of: substitution step
definition: The stereospecific oxidation of a (phenyldimethylsilyl)alkane to the corresponding alcohol using bromine, usually generated in situ from potassium bromide and peracetic acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r150/
has_exact_synonym: Fleming oxidation
has_exact_synonym: Tamao-Fleming oxidation
has_obo_namespace: RXNO
id: RXNO:0000210

Axiom
annotated source: Fleming-Tamao oxidation
annotated property: definition
annotated target: The stereospecific oxidation of a (phenyldimethylsilyl)alkane to the corresponding alcohol using bromine, usually generated in situ from potassium bromide and peracetic acid.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Tamao oxidation
type: Class
subclass of: substitution step
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular substitution objective
subclass of: Restriction
  on property: has specified reactant
  some values from: hydrogen peroxide
definition: The stereospecific oxidation of a (halosilyl)alkane to the corresponding alcohol using potassium fluoride and hydrogen peroxide.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r150/
has_exact_synonym: Tamao-Kumada oxidation
has_obo_namespace: RXNO
id: RXNO:0000211

Axiom
annotated source: Tamao oxidation
annotated property: definition
annotated target: The stereospecific oxidation of a (halosilyl)alkane to the corresponding alcohol using potassium fluoride and hydrogen peroxide.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Sakurai reaction, aldehyde or ketone
type: Class
equivalent class: Class
  union of: aldehyde Sakurai reaction
  union of: ketone Sakurai reaction
subclass of: molecular skeleton joining reaction
subclass of: Sakurai reaction
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular skeleton joining objective
definition: A carbon-carbon coupling reaction in which an aldehyde or ketone reacts with allyltrimethylsilane to form a homoallylic alcohol.
has_obo_namespace: RXNO
id: RXNO:0000212

Axiom
annotated source: Sakurai reaction, aldehyde or ketone
annotated property: definition
annotated target: A carbon-carbon coupling reaction in which an aldehyde or ketone reacts with allyltrimethylsilane to form a homoallylic alcohol.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Sakurai reaction, enone
type: Class
subclass of: Sakurai reaction
definition: A carbon-carbon coupling reaction in which an enone reacts with allyltrimethylsilane to form a delta,epsilon-unsaturated carbonyl compound.
has_obo_namespace: RXNO
id: RXNO:0000213

Axiom
annotated source: Sakurai reaction, enone
annotated property: definition
annotated target: A carbon-carbon coupling reaction in which an enone reacts with allyltrimethylsilane to form a delta,epsilon-unsaturated carbonyl compound.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Sakurai reaction, acid chloride
type: Class
subclass of: Sakurai reaction
definition: A carbon-carbon coupling reaction in which an acid chloride reacts with allyltrimethylsilane to form a gamma,delta-unsaturated ketone.
has_obo_namespace: RXNO
id: RXNO:0000214

Axiom
annotated source: Sakurai reaction, acid chloride
annotated property: definition
annotated target: A carbon-carbon coupling reaction in which an acid chloride reacts with allyltrimethylsilane to form a gamma,delta-unsaturated ketone.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Sakurai reaction, acetal or ketal
type: Class
subclass of: Sakurai reaction
definition: A carbon-carbon coupling reaction in which an acetal or ketal reacts with allyltrimethylsilane to form a homoallylic ether.
has_obo_namespace: RXNO
id: RXNO:0000215

Axiom
annotated source: Sakurai reaction, acetal or ketal
annotated property: definition
annotated target: A carbon-carbon coupling reaction in which an acetal or ketal reacts with allyltrimethylsilane to form a homoallylic ether.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

imine Sakurai reaction
type: Class
subclass of: Sakurai reaction
definition: A carbon-carbon coupling reaction in which an imine reacts with allyltrimethylsilane to form a homoallylic amine.
has_obo_namespace: RXNO
id: RXNO:0000216

Axiom
annotated source: imine Sakurai reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction in which an imine reacts with allyltrimethylsilane to form a homoallylic amine.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Sakurai reaction, epoxide
type: Class
subclass of: ring breaking
subclass of: Sakurai reaction
definition: A ring-breaking reaction in which an epoxide reacts with allyltrimethylsilane to form a hydroxy alkene.
has_obo_namespace: RXNO
id: RXNO:0000217

Axiom
annotated source: Sakurai reaction, epoxide
annotated property: definition
annotated target: A ring-breaking reaction in which an epoxide reacts with allyltrimethylsilane to form a hydroxy alkene.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Cannizzaro reaction
type: Class
subclass of: functional group modification
subclass of: Restriction
  on property: has specified product
  some values from: alcohol
subclass of: Restriction
  on property: has specified product
  some values from: carboxylic acid
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: The disproportionation of a non-enolisable aldehyde to the corresponding carboxylic acid and alcohol. The reaction is base-catalysed.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r71/
has_obo_namespace: RXNO
id: RXNO:0000218

Axiom
annotated source: Cannizzaro reaction
annotated property: definition
annotated target: The disproportionation of a non-enolisable aldehyde to the corresponding carboxylic acid and alcohol. The reaction is base-catalysed.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

crossed Cannizzaro reaction
type: Class
subclass of: functional group modification
subclass of: Restriction
  on property: has specified product
  some values from: alcohol
subclass of: Restriction
  on property: has specified product
  some values from: carboxylic acid
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: The reaction between two different non-enolisable aldehydes to give a carboxylic acid and an alcohol. The reaction is base-catalysed.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r71/
has_obo_namespace: RXNO
id: RXNO:0000219

Axiom
annotated source: crossed Cannizzaro reaction
annotated property: definition
annotated target: The reaction between two different non-enolisable aldehydes to give a carboxylic acid and an alcohol. The reaction is base-catalysed.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Pummerer rearrangement
type: Class
subclass of: functional group modification
definition: The conversion of a sulfoxide with an alpha-hydrogen to an alpha-substituted thioether. The reaction is usually performed with an acid anhydride or acyl halide.
has_exact_synonym: Pummerer methyl sulfoxide rearrangement
has_obo_namespace: RXNO
id: RXNO:0000220

Axiom
annotated source: Pummerer rearrangement
annotated property: definition
annotated target: The conversion of a sulfoxide with an alpha-hydrogen to an alpha-substituted thioether. The reaction is usually performed with an acid anhydride or acyl halide.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Polonovski reaction
type: Class
subclass of: cleaving reaction
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
definition: The reaction of a tertiary amine oxide with an anhydride or acyl chloride to give an N,N-disubstituted acetamide and an aldehyde.
has_obo_namespace: RXNO
id: RXNO:0000221

Axiom
annotated source: Polonovski reaction
annotated property: definition
annotated target: The reaction of a tertiary amine oxide with an anhydride or acyl chloride to give an N,N-disubstituted acetamide and an aldehyde.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Polonovski-Potier reaction
type: Class
subclass of: Polonovski reaction
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
definition: The reaction of a tertiary amine oxide with trifluoroacetic anhydride to give an N,N-disubstituted acetamide and an aldehyde.
has_exact_synonym: Potier-Polonovski reaction
has_obo_namespace: RXNO
id: RXNO:0000222

Axiom
annotated source: Polonovski-Potier reaction
annotated property: definition
annotated target: The reaction of a tertiary amine oxide with trifluoroacetic anhydride to give an N,N-disubstituted acetamide and an aldehyde.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Menshutkin reaction
type: Class
subclass of: N-alkylation
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified reactant
  some values from: tertiary amine
definition: The alkylation of a tertiary amine with an alkyl halide to the corresponding ammonium salt.
has_alternative_id: RXNO:0000375
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r275/
has_exact_synonym: Menschutkin reaction
has_obo_namespace: RXNO
id: RXNO:0000223

Axiom
annotated source: Menshutkin reaction
annotated property: definition
annotated target: The alkylation of a tertiary amine with an alkyl halide to the corresponding ammonium salt.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Strecker degradation
type: Class
subclass of: end-of-chain chain shortening
definition: The deamination and decarboxylation of amino acids to imines and then to aldehydes or ketones, in the presence of a carbonyl compound (especially an alpha,beta-dicarbonyl compound or a reducing sugar such as glucose). The reaction is involved in the generation of meat aromas/flavours in cooking.
has_obo_namespace: RXNO
id: RXNO:0000224

Axiom
annotated source: Strecker degradation
annotated property: definition
annotated target: The deamination and decarboxylation of amino acids to imines and then to aldehydes or ketones, in the presence of a carbonyl compound (especially an alpha,beta-dicarbonyl compound or a reducing sugar such as glucose). The reaction is involved in the generation of meat aromas/flavours in cooking.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Wohl-Ziegler bromination
type: Class
subclass of: functional group addition step
definition: The allylic or benzylic bromination of hydrocarbons using an N-bromoimide and a radical initiator, to give an allylic or benzylic bromide.
has_exact_synonym: Wohl-Ziegler reaction
has_obo_namespace: RXNO
id: RXNO:0000225

Axiom
annotated source: Wohl-Ziegler bromination
annotated property: definition
annotated target: The allylic or benzylic bromination of hydrocarbons using an N-bromoimide and a radical initiator, to give an allylic or benzylic bromide.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Wolff-Kishner reduction
type: Class
subclass of: functional group reduction
definition: The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base.
has_obo_namespace: RXNO
id: RXNO:0000226

Axiom
annotated source: Wolff-Kishner reduction
annotated property: definition
annotated target: The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Wolff-Kishner reduction, Huang-Minlon modification
type: Class
subclass of: Wolff-Kishner reduction
definition: The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base in refluxing ethylene glycol.
has_exact_synonym: Huang-Minlon modification
has_obo_namespace: RXNO
id: RXNO:0000227

Axiom
annotated source: Wolff-Kishner reduction, Huang-Minlon modification
annotated property: definition
annotated target: The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base in refluxing ethylene glycol.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Zemplen transesterification
type: Class
subclass of: functional group reduction
definition: The reduction of an ester to the corresponding alcohol, using sodium methoxide in dry methanol.
has_exact_synonym: Zemplen procedure
has_obo_namespace: RXNO
id: RXNO:0000228

Axiom
annotated source: Zemplen transesterification
annotated property: definition
annotated target: The reduction of an ester to the corresponding alcohol, using sodium methoxide in dry methanol.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Ferrier rearrangement
type: Class
subclass of: rearrangement step
definition: The rearrangement of an O-alkenyl acetal to give the corresponding beta-alkoxy carbonyl compound.
has_exact_synonym: Ferrier reaction
has_obo_namespace: RXNO
id: RXNO:0000229

Axiom
annotated source: Ferrier rearrangement
annotated property: definition
annotated target: The rearrangement of an O-alkenyl acetal to give the corresponding beta-alkoxy carbonyl compound.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

aza-Ferrier rearrangement
type: Class
subclass of: rearrangement step
definition: The rearrangement of an O-alkenyl hemiaminal ether to give the corresponding beta-amino carbonyl compound.
has_exact_synonym: aza-Ferrier reaction
has_obo_namespace: RXNO
id: RXNO:0000230

Axiom
annotated source: aza-Ferrier rearrangement
annotated property: definition
annotated target: The rearrangement of an O-alkenyl hemiaminal ether to give the corresponding beta-amino carbonyl compound.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

aza-ene reaction
type: Class
subclass of: molecular skeleton joining reaction
definition: A joining reaction where an N=C system with an allylic hydrogen reacts with a compound containing a multiple bond (an enophile) to form a substituted alkene.
has_obo_namespace: RXNO
id: RXNO:0000231

Axiom
annotated source: aza-ene reaction
annotated property: definition
annotated target: A joining reaction where an N=C system with an allylic hydrogen reacts with a compound containing a multiple bond (an enophile) to form a substituted alkene.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Petasis reaction
type: Class
subclass of: functional group modification
subclass of: Restriction
  on property: has specified product
  some values from: amine
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: amine
subclass of: Restriction
  on property: has specified reactant
  some values from: boronic acids
definition: The alkylation of an amine with a boronic acid and an aldehyde to give a substituted amine.
has_exact_synonym: Petasis three-component coupling
has_obo_namespace: RXNO
id: RXNO:0000232

Axiom
annotated source: Petasis reaction
annotated property: definition
annotated target: The alkylation of an amine with a boronic acid and an aldehyde to give a substituted amine.
database_cross_reference: RSC:db

Achmatowicz rearrangement
type: Class
subclass of: ring rearrangement
definition: A rearrangement of a furfuryl alcohol derivative to a dihydropyranone, from which monosaccharides may be synthesised.
has_obo_namespace: RXNO
id: RXNO:0000233

Axiom
annotated source: Achmatowicz rearrangement
annotated property: definition
annotated target: A rearrangement of a furfuryl alcohol derivative to a dihydropyranone, from which monosaccharides may be synthesised.
database_cross_reference: RSC:db

aza-Achmatowicz rearrangement
type: Class
subclass of: ring rearrangement
definition: A rearrangement of a furfuryl amine derivative to a tetrahydropyridinone.
has_obo_namespace: RXNO
id: RXNO:0000234

Axiom
annotated source: aza-Achmatowicz rearrangement
annotated property: definition
annotated target: A rearrangement of a furfuryl amine derivative to a tetrahydropyridinone.
database_cross_reference: RSC:db

aza-Henry reaction
type: Class
subclass of: carbon-carbon coupling reaction
definition: A carbon-carbon coupling reaction between a nitroalkane and an imine to give a beta-amino nitroalkane.
has_obo_namespace: RXNO
id: RXNO:0000235

Axiom
annotated source: aza-Henry reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction between a nitroalkane and an imine to give a beta-amino nitroalkane.
database_cross_reference: RSC:db

Biginelli reaction
type: Class
subclass of: molecular dehydration reaction
subclass of: ring formation reaction step
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: A three-component coupling of a beta-keto ester, an aldehyde and urea to give a 3,4-dihydropyrimidinone.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r43/
has_exact_synonym: Biginelli condensation
has_exact_synonym: Biginelli pyrimidone synthesis
has_exact_synonym: Biginelli three-component reaction
has_obo_namespace: RXNO
id: RXNO:0000236

Axiom
annotated source: Biginelli reaction
annotated property: definition
annotated target: A three-component coupling of a beta-keto ester, an aldehyde and urea to give a 3,4-dihydropyrimidinone.
database_cross_reference: RSC:db

Blaise reaction
type: Class
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has_catalyst
  some values from: zinc atom
definition: The coupling of an alpha-bromo ester with a nitrile to give a beta-ketoester, in the presence of zinc.
has_obo_namespace: RXNO
id: RXNO:0000237

Axiom
annotated source: Blaise reaction
annotated property: definition
annotated target: The coupling of an alpha-bromo ester with a nitrile to give a beta-ketoester, in the presence of zinc.
database_cross_reference: RSC:db

Katritzky pyrylium-pyridinium method
type: Class
subclass of: substitution step
definition: The substitution of an amine with a nucleophile using a pyrylium salt.
has_obo_namespace: RXNO
id: RXNO:0000238

Axiom
annotated source: Katritzky pyrylium-pyridinium method
annotated property: definition
annotated target: The substitution of an amine with a nucleophile using a pyrylium salt.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

metalla-aza-Claisen rearrangement
type: Class
subclass of: rearrangement step
definition: The rearrangement of a 3-aza-4-metalla-1,5-hexadiene to form a delta,epsilon-unsaturated metallaimine.
has_obo_namespace: RXNO
id: RXNO:0000239

Axiom
annotated source: metalla-aza-Claisen rearrangement
annotated property: definition
annotated target: The rearrangement of a 3-aza-4-metalla-1,5-hexadiene to form a delta,epsilon-unsaturated metallaimine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Bergman cyclisation
type: Class
subclass of: ring formation reaction step
definition: The cyclisation of an ene-diyne to give a 1,4-diradical cyclohexatriene. The diradical usually aromatises.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r37/
has_exact_synonym: Bergman cyclization
has_exact_synonym: Bergman reaction
has_exact_synonym: Masamune-Bergman cyclisation
has_exact_synonym: Masamune-Bergman cyclization
has_obo_namespace: RXNO
id: RXNO:0000240

Axiom
annotated source: Bergman cyclisation
annotated property: definition
annotated target: The cyclisation of an ene-diyne to give a 1,4-diradical cyclohexatriene. The diradical usually aromatises.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

nitro-Michael reaction
type: Class
subclass of: Michael addition
definition: A conjugate addition reaction where a carbon nucleophile adds to an alpha,beta-unsaturated nitro compound.
has_obo_namespace: RXNO
id: RXNO:0000241

Axiom
annotated source: nitro-Michael reaction
annotated property: definition
annotated target: A conjugate addition reaction where a carbon nucleophile adds to an alpha,beta-unsaturated nitro compound.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Noyori asymmetric hydrogenation, alkene
type: Class
subclass of: addition reaction step
definition: The homogeneous asymmetric catalytic hydrogenation of a C=C double bond using a ruthenium(II) BINAP catalyst.
has_exact_synonym: Noyori hydrogenation, alkene
has_obo_namespace: RXNO
id: RXNO:0000242

Axiom
annotated source: Noyori asymmetric hydrogenation, alkene
annotated property: definition
annotated target: The homogeneous asymmetric catalytic hydrogenation of a C=C double bond using a ruthenium(II) BINAP catalyst.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Noyori asymmetric hydrogenation, carbonyl
type: Class
subclass of: functional group reduction
definition: The homogeneous asymmetric catalytic hydrogenation of a carbonyl bond using a ruthenium(II) BINAP catalyst.
has_exact_synonym: Noyori hydrogenation, carbonyl
has_obo_namespace: RXNO
id: RXNO:0000243

Axiom
annotated source: Noyori asymmetric hydrogenation, carbonyl
annotated property: definition
annotated target: The homogeneous asymmetric catalytic hydrogenation of a carbonyl bond using a ruthenium(II) BINAP catalyst.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Passerini reaction
type: Class
subclass of: molecular skeleton joining reaction
definition: The reaction between an isonitrile, a carboxylic acid and aldehyde or ketone to give an alpha-acyloxy amide.
has_obo_namespace: RXNO
id: RXNO:0000244

Axiom
annotated source: Passerini reaction
annotated property: definition
annotated target: The reaction between an isonitrile, a carboxylic acid and aldehyde or ketone to give an alpha-acyloxy amide.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

ring-closing metathesis
type: Class
subclass of: ring formation reaction step
definition: A joining reaction in which two carbon-carbon double bonds in the same molecule are redistributed to give a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene.
has_exact_synonym: RCM
has_exact_synonym: ring closing alkene metathesis
has_exact_synonym: ring closing metathesis
has_exact_synonym: ring closing olefin metathesis
has_exact_synonym: ring-closing alkene metathesis
has_exact_synonym: ring-closing olefin metathesis
has_obo_namespace: RXNO
id: RXNO:0000245

Axiom
annotated source: ring-closing metathesis
annotated property: definition
annotated target: A joining reaction in which two carbon-carbon double bonds in the same molecule are redistributed to give a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

polymerisation reaction
type: Class
equivalent class: Class
  intersection of: molecular skeleton joining reaction
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: polymerisation objective
  intersection of: Restriction
    on property: has specified product
    some values from: macromolecule
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: polymerisation objective
subclass of: Restriction
  on property: has specified product
  some values from: macromolecule
definition: A joining reaction, the objective of which is that a large number of monomers react together to produce a polymer consisting of repeating units.
has_exact_synonym: polymerisation
has_exact_synonym: polymerization
has_exact_synonym: polymerization reaction
has_obo_namespace: RXNO
id: RXNO:0000246

Axiom
annotated source: polymerisation reaction
annotated property: definition
annotated target: A joining reaction, the objective of which is that a large number of monomers react together to produce a polymer consisting of repeating units.
database_cross_reference: rsc:db

ring-opening metathesis polymerisation
type: Class
subclass of: polymerisation reaction
definition: A joining reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. two alkenes. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of ring strain in the cycloalkene.
has_exact_synonym: ROMP
has_exact_synonym: ring-opening metathesis polymerization
has_obo_namespace: RXNO
id: RXNO:0000247

Axiom
annotated source: ring-opening metathesis polymerisation
annotated property: definition
annotated target: A joining reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. two alkenes. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of ring strain in the cycloalkene.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

Carroll rearrangement
type: Class
subclass of: rearrangement step
definition: An adaptation of the Claisen rearrangement that transforms a beta-keto allyl ester into a gamma,delta-allyl ketone. It uses base and high temperature or milder conditions with a ruthenium or palladium complex as catalyst.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r72/
has_exact_synonym: Kimel-Cope rearrangement
has_obo_namespace: RXNO
id: RXNO:0000248

Axiom
annotated source: Carroll rearrangement
annotated property: definition
annotated target: An adaptation of the Claisen rearrangement that transforms a beta-keto allyl ester into a gamma,delta-allyl ketone. It uses base and high temperature or milder conditions with a ruthenium or palladium complex as catalyst.
database_cross_reference: RSC:db

Bose-Mitsunobu reaction
type: Class
subclass of: Mitsunobu reaction
definition: A Mitsunobu reaction, where an alcohol is converted to something else with inversion at the stereocentre, using diphenylphosphoryl azide.
has_obo_namespace: RXNO
id: RXNO:0000249

Axiom
annotated source: Bose-Mitsunobu reaction
annotated property: definition
annotated target: A Mitsunobu reaction, where an alcohol is converted to something else with inversion at the stereocentre, using diphenylphosphoryl azide.
database_cross_reference: RSC:db

Fritsch-Buttenberg-Wiechell rearrangement
type: Class
subclass of: rearrangement step
subclass of: Restriction
  on property: has specified product
  some values from: acetylenic compound
definition: The rearrangement of a 2-bromoalkene into an alkyne, mediated by strong base.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r161/
database_cross_reference: https://www.wikidata.org/wiki/Q573664
has_obo_namespace: RXNO
id: RXNO:0000250

Axiom
annotated source: Fritsch-Buttenberg-Wiechell rearrangement
annotated property: definition
annotated target: The rearrangement of a 2-bromoalkene into an alkyne, mediated by strong base.
database_cross_reference: RSC:db

Stork-Wittig olefination
type: Class
subclass of: olefination
subclass of: Restriction
  on property: has specified product
  some values from: olefin
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: A carbon-carbon coupling reaction where an aldehyde reacts with a phosphonium salt to give a Z-iodoalkene. The reaction is mediated by sodium or potassium hexamethyldisilazide.
has_obo_namespace: RXNO
id: RXNO:0000251

Axiom
annotated source: Stork-Wittig olefination
annotated property: definition
annotated target: A carbon-carbon coupling reaction where an aldehyde reacts with a phosphonium salt to give a Z-iodoalkene. The reaction is mediated by sodium or potassium hexamethyldisilazide.
database_cross_reference: RSC:db

Cadogan carbazole synthesis
type: Class
subclass of: carbazole synthesis
subclass of: Restriction
  on property: has specified product
  some values from: carbazoles
definition: The reduction of a 2-nitrobiaryl compound to give a carbazole.
has_obo_namespace: RXNO
id: RXNO:0000252

Axiom
annotated source: Cadogan carbazole synthesis
annotated property: definition
annotated target: The reduction of a 2-nitrobiaryl compound to give a carbazole.
database_cross_reference: doi:10.1039/JR9650004831
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Cadogan coupling
type: Class
subclass of: carbon-carbon coupling reaction
definition: The arylation of an arylamine mediated by isopentyl nitrite.
has_obo_namespace: RXNO
id: RXNO:0000253

Axiom
annotated source: Cadogan coupling
annotated property: definition
annotated target: The arylation of an arylamine mediated by isopentyl nitrite.
database_cross_reference: doi:10.1039/b409373a
database_cross_reference: https://orcid.org/0000-0002-4077-4719

MacDonald condensation
type: Class
subclass of: fused-ring-system formation
definition: The reaction between a 1,9-diformyldipyrromethane and a dipyrromethane to give a porphodimethene.
has_obo_namespace: RXNO
id: RXNO:0000254

Axiom
annotated source: MacDonald condensation
annotated property: definition
annotated target: The reaction between a 1,9-diformyldipyrromethane and a dipyrromethane to give a porphodimethene.
database_cross_reference: doi:10.1039/a908784b
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Zweifel diene synthesis
type: Class
subclass of: carbon-carbon homocoupling reaction
definition: The carbon-carbon homocoupling reaction of a pair of alkyne molecules using a borane and iodine. The reaction proceeds via a borane intermediate.
has_obo_namespace: RXNO
id: RXNO:0000255

Axiom
annotated source: Zweifel diene synthesis
annotated property: definition
annotated target: The carbon-carbon homocoupling reaction of a pair of alkyne molecules using a borane and iodine. The reaction proceeds via a borane intermediate.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: isbn:9780521096430

Dess-Martin oxidation
type: Class
subclass of: alcohol oxidation
subclass of: functional group oxidation
definition: The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using the Dess-Martin periodinane.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r107/
database_cross_reference: https://www.wikidata.org/wiki/Q28455131
has_exact_synonym: Dess-Martin periodinane oxidation
has_obo_namespace: RXNO
id: RXNO:0000256

Axiom
annotated source: Dess-Martin oxidation
annotated property: definition
annotated target: The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using the Dess-Martin periodinane.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Criegee oxidation
type: Class
subclass of: cleaving reaction
subclass of: alkene oxidative cleavage
definition: The oxidative cleavage of an alpha,beta-diol using lead tetraacetate to give the corresponding carbonyl compounds.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r96/
database_cross_reference: https://www.wikidata.org/wiki/Q30693026
has_exact_synonym: Criegee glycol cleavage
has_exact_synonym: Criegee reaction
has_obo_namespace: RXNO
id: RXNO:0000257

Axiom
annotated source: Criegee oxidation
annotated property: definition
annotated target: The oxidative cleavage of an alpha,beta-diol using lead tetraacetate to give the corresponding carbonyl compounds.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Simmons-Smith reaction
type: Class
subclass of: ring formation reaction step
subclass of: Restriction
  on property: has specified product
  some values from: cyclopropanes
subclass of: Restriction
  on property: has specified reactant
  some values from: olefin
definition: A ring formation reaction where an alkene reacts with a dihalomethane in the presence of a metal atom or metal complexes to form a cyclopropane. The traditional reaction uses a zinc-copper couple and diiodomethane.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r400/
database_cross_reference: https://www.wikidata.org/wiki/Q903776
has_exact_synonym: Simmons-Smith cyclopropanation
has_obo_namespace: RXNO
id: RXNO:0000258

Axiom
annotated source: Simmons-Smith reaction
annotated property: definition
annotated target: A ring formation reaction where an alkene reacts with a dihalomethane in the presence of a metal atom or metal complexes to form a cyclopropane. The traditional reaction uses a zinc-copper couple and diiodomethane.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Wittig rearrangement
type: Class
subclass of: rearrangement step
definition: Any of a family of sigmatropic rearrangements that involve the migration of a group on an electronegative atom (O or N) to a carbon atom.
has_obo_namespace: RXNO
id: RXNO:0000259

Axiom
annotated source: Wittig rearrangement
annotated property: definition
annotated target: Any of a family of sigmatropic rearrangements that involve the migration of a group on an electronegative atom (O or N) to a carbon atom.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

[1,2]-Wittig rearrangement
type: Class
subclass of: Wittig rearrangement
subclass of: Restriction
  on property: has specified product
  some values from: alcohol
subclass of: Restriction
  on property: has specified reactant
  some values from: ether
definition: A base-mediated 1,2-sigmatropic rearrangement of an ether to give an alcohol.
has_exact_synonym: 1,2-Wittig rearrangement
has_exact_synonym: [1,2] Wittig rearrangement
has_obo_namespace: RXNO
id: RXNO:0000260

Axiom
annotated source: [1,2]-Wittig rearrangement
annotated property: definition
annotated target: A base-mediated 1,2-sigmatropic rearrangement of an ether to give an alcohol.
database_cross_reference: rsc:db

[2,3]-Wittig rearrangement
type: Class
subclass of: Wittig rearrangement
definition: A base-mediated 2,3-sigmatropic rearrangement of an allyl ether to give a homoallylic alcohol.
has_exact_synonym: 2,3-Wittig rearrangement
has_exact_synonym: [2,3] Wittig rearrangement
has_obo_namespace: RXNO
id: RXNO:0000261

Axiom
annotated source: [2,3]-Wittig rearrangement
annotated property: definition
annotated target: A base-mediated 2,3-sigmatropic rearrangement of an allyl ether to give a homoallylic alcohol.
database_cross_reference: rsc:db

[1,2]-aza-Wittig rearrangement
type: Class
subclass of: Wittig rearrangement
subclass of: Restriction
  on property: has specified product
  some values from: secondary amine
subclass of: Restriction
  on property: has specified reactant
  some values from: tertiary amine
definition: A base-mediated 1,2-sigmatropic rearrangement of a tertiary amine to give a secondary amine.
has_exact_synonym: 1,2-aza-Wittig rearrangement
has_exact_synonym: [1,2] aza-Wittig rearrangement
has_obo_namespace: RXNO
id: RXNO:0000262

Axiom
annotated source: [1,2]-aza-Wittig rearrangement
annotated property: definition
annotated target: A base-mediated 1,2-sigmatropic rearrangement of a tertiary amine to give a secondary amine.
database_cross_reference: rsc:db

[2,3]-aza-Wittig rearrangement
type: Class
subclass of: Wittig rearrangement
definition: A base-mediated 2,3-sigmatropic rearrangement of an activated tertiary allyl amine, to give a secondary homoallylic amine.
has_exact_synonym: 2,3-aza-Wittig rearrangement
has_exact_synonym: [2,3] aza-Wittig rearrangement
has_obo_namespace: RXNO
id: RXNO:0000263

Axiom
annotated source: [2,3]-aza-Wittig rearrangement
annotated property: definition
annotated target: A base-mediated 2,3-sigmatropic rearrangement of an activated tertiary allyl amine, to give a secondary homoallylic amine.
database_cross_reference: rsc:db

aza-Baylis-Hillman reaction
type: Class
subclass of: Baylis-Hillman reaction
definition: A carbon-carbon coupling of an imine to an activated alkene in the presence of a nucleophilic base to give an allylic amine.
has_exact_synonym: aza-Morita-Baylis-Hillman reaction
has_obo_namespace: RXNO
id: RXNO:0000264

Axiom
annotated source: aza-Baylis-Hillman reaction
annotated property: definition
annotated target: A carbon-carbon coupling of an imine to an activated alkene in the presence of a nucleophilic base to give an allylic amine.
database_cross_reference: rsc:db

aza-Wittig reaction
type: Class
subclass of: carbonyl compound to imine conversion
definition: Reaction of a carbonyl compound with a phosphazene to give an imine.
has_obo_namespace: RXNO
id: RXNO:0000265

Axiom
annotated source: aza-Wittig reaction
annotated property: definition
annotated target: Reaction of a carbonyl compound with a phosphazene to give an imine.
database_cross_reference: rsc:db

Fenton reaction
type: Class
equivalent class: Class
  union of: Fenton 1,2-glycol oxidation
  union of: Fenton alpha-hydroxy carboxylic acid oxidation
  union of: Fenton hydrogen peroxide reduction
subclass of: functional group oxidation
definition: An oxidation reaction involving Fenton's reagent.
has_alternative_id: RXNO:0000267
has_exact_synonym: Fenton's reaction
has_obo_namespace: RXNO
id: RXNO:0000266

Axiom
annotated source: Fenton reaction
annotated property: definition
annotated target: An oxidation reaction involving Fenton's reagent.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

RXNO_0000267
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: Fenton reaction
deprecated: true

Hantzsch pyridine synthesis
type: Class
subclass of: pyridine synthesis
subclass of: Restriction
  on property: has specified product
  some values from: dihydropyridine
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: A ring-forming reaction between two equivalents of a beta-ketoester, an aldehyde and ammonia (or an ammonium salt), to give a dihydropyridine. The dihydropyridine can be oxidised to a pyridine using an oxidising agent.
has_exact_synonym: Hantzsch dihydropyridine synthesis
has_obo_namespace: RXNO
id: RXNO:0000268

Axiom
annotated source: Hantzsch pyridine synthesis
annotated property: definition
annotated target: A ring-forming reaction between two equivalents of a beta-ketoester, an aldehyde and ammonia (or an ammonium salt), to give a dihydropyridine. The dihydropyridine can be oxidised to a pyridine using an oxidising agent.
database_cross_reference: rsc:db

alkyne-azide click reaction
type: Class
subclass of: [3+2] cycloaddition
subclass of: 1,3-dipolar cycloaddition
subclass of: Restriction
  on property: has specified product
  some values from: 1,2,3-triazole
subclass of: Restriction
  on property: has specified reactant
  some values from: azide
subclass of: Restriction
  on property: has specified reactant
  some values from: acetylenic compound
definition: A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole, needing only heat to proceed.
has_broad_synonym: Huisgen cycloaddition
has_broad_synonym: Huisgen reaction
has_broad_synonym: Huisgen's 1,3-dipolar cycloaddition
has_exact_synonym: "click" reaction
has_exact_synonym: 'click' reaction
has_exact_synonym: alkyne-azide Huisgen cycloaddition
has_exact_synonym: alkyne-azide Huisgen reaction
has_exact_synonym: azide-alkyne Huisgen cycloaddition
has_exact_synonym: azide-alkyne Huisgen reaction
has_exact_synonym: azide-alkyne click reaction
has_exact_synonym: click reaction
has_obo_namespace: RXNO
id: RXNO:0000269
comment: Note: The term "click reaction" was originally used in a broader sense to refer to any coupling that took place cleanly and quickly in quantitative yield, but it now always seems to be used in this narrower sense.

Axiom
annotated source: alkyne-azide click reaction
annotated property: definition
annotated target: A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole, needing only heat to proceed.
database_cross_reference: rsc:db

copper(I)-catalyzed azide-alkyne cycloaddition
type: Class
subclass of: [3+2] cycloaddition
subclass of: Restriction
  on property: has specified product
  some values from: 1,2,3-triazole
subclass of: Restriction
  on property: has specified reactant
  some values from: azide
subclass of: Restriction
  on property: has specified reactant
  some values from: acetylenic compound
definition: A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole as a single regioisomer.
has_exact_synonym: CuAAC
has_exact_synonym: copper(I)-catalysed alkyne-azide cycloaddition
has_exact_synonym: copper(I)-catalysed azide-alkyne click reaction
has_exact_synonym: copper(I)-catalysed azide-alkyne cycloaddition
has_exact_synonym: copper(I)-catalyzed alkyne-azide cycloaddition
has_exact_synonym: copper(I)-catalyzed azide-alkyne click reaction
has_exact_synonym: copper(I)-catalyzed azide-alkyne cycloaddition
has_obo_namespace: RXNO
id: RXNO:0000270
comment: Commonly described as a variant of the (uncatalyzed) alkyne-azide click reaction, the mechanism of reaction is different, and thus formally it is not a 1,3-dipolar cycloaddition. [rsc:db]

Axiom
annotated source: copper(I)-catalyzed azide-alkyne cycloaddition
annotated property: definition
annotated target: A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole as a single regioisomer.
database_cross_reference: RSC:db

Fischer-Tropsch process
type: Class
subclass of: molecular skeleton joining reaction
definition: A process in which carbon monoxide and hydrogen ('syngas') are converted into various liquid hydrocarbons.
has_exact_synonym: Fischer-Tropsch reaction
has_exact_synonym: Fischer-Tropsch synthesis
has_obo_namespace: RXNO
id: RXNO:0000271

Axiom
annotated source: Fischer-Tropsch process
annotated property: definition
annotated target: A process in which carbon monoxide and hydrogen ('syngas') are converted into various liquid hydrocarbons.
database_cross_reference: rsc:db

hydroformylation
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
definition: The reaction of hydrogen and carbon monoxide with an alkene, to give an aldehyde, catalysed by a rhodium or cobalt catalyst. The process is equivalent to the formal addition of the H-C bond of formaldehyde across the double bond of an alkene.
has_obo_namespace: RXNO
id: RXNO:0000272

Axiom
annotated source: hydroformylation
annotated property: definition
annotated target: The reaction of hydrogen and carbon monoxide with an alkene, to give an aldehyde, catalysed by a rhodium or cobalt catalyst. The process is equivalent to the formal addition of the H-C bond of formaldehyde across the double bond of an alkene.
database_cross_reference: rsc:db

retro-Diels-Alder reaction
type: Class
subclass of: ring breaking
subclass of: Restriction
  on property: has specified reactant
  some values from: cyclohexadiene
definition: The reverse of a [4+2] cycloaddition reaction, in which an unsaturated six-membered ring compound fragments to give a diene and a compound containing a double or triple bond (a dienophile).
has_exact_synonym: retro Diels-Alder reaction
has_obo_namespace: RXNO
id: RXNO:0000273

Axiom
annotated source: retro-Diels-Alder reaction
annotated property: definition
annotated target: The reverse of a [4+2] cycloaddition reaction, in which an unsaturated six-membered ring compound fragments to give a diene and a compound containing a double or triple bond (a dienophile).
database_cross_reference: rsc:db

retro-aldol addition
type: Class
subclass of: cleaving reaction
definition: The reverse of an aldol addition, in which a beta-hydroxy ketone fragments to form a carbonyl compound and the enolate of an alpha-acidic carbonyl compound.
has_exact_synonym: retro-aldol reaction
has_obo_namespace: RXNO
id: RXNO:0000274
comment: This process can occur because the whole reaction is an equilibrium. In the forward direction (aldol addition), elimination of water from the beta-hydroxy ketone, giving an alpha,beta-unsaturated ketone, is irreversible, and thus the aldol condensation does not have a "retro" counterpart.

Axiom
annotated source: retro-aldol addition
annotated property: definition
annotated target: The reverse of an aldol addition, in which a beta-hydroxy ketone fragments to form a carbonyl compound and the enolate of an alpha-acidic carbonyl compound.
database_cross_reference: rsc:db

Stork-Crabtree hydrogenation
type: Class
subclass of: addition reaction step
definition: A hydrogenation in which a metal-ligating group distant from the reacting alkene directs the attack of hydrogen, giving preferentially one stereoisomer of the product.
has_obo_namespace: RXNO
id: RXNO:0000275

Axiom
annotated source: Stork-Crabtree hydrogenation
annotated property: definition
annotated target: A hydrogenation in which a metal-ligating group distant from the reacting alkene directs the attack of hydrogen, giving preferentially one stereoisomer of the product.
database_cross_reference: doi:10.1021/jo00364a007
database_cross_reference: rsc:db

Aufbau reaction
type: Class
subclass of: polymerisation reaction
definition: The insertion of alkenes (usually ethene) into the Al-C bond of an aluminium alkyl, to give a long-chain aluminium alkyl that can go on to react again, or can decompose into the corresponding terminal alkene. The addition of transition metals results in reliable production of high molecular weight polymers.
has_exact_synonym: "Aufbau" reaction
has_exact_synonym: 'Aufbau' reaction
has_exact_synonym: Aufbau process
has_obo_namespace: RXNO
id: RXNO:0000276

Axiom
annotated source: Aufbau reaction
annotated property: definition
annotated target: The insertion of alkenes (usually ethene) into the Al-C bond of an aluminium alkyl, to give a long-chain aluminium alkyl that can go on to react again, or can decompose into the corresponding terminal alkene. The addition of transition metals results in reliable production of high molecular weight polymers.
database_cross_reference: rsc:db

hydroalumination
type: Class
subclass of: hydrometallation
definition: The reaction of an aluminium alkyl with an alkene, to give an intermediate aluminium species that can give various products after work-up.
has_obo_namespace: RXNO
id: RXNO:0000277

Axiom
annotated source: hydroalumination
annotated property: definition
annotated target: The reaction of an aluminium alkyl with an alkene, to give an intermediate aluminium species that can give various products after work-up.
database_cross_reference: rsc:db

hydrovinylation
type: Class
subclass of: carbon-carbon coupling reaction
definition: The reaction of two alkenes to give an elongated alkene, employing a transition-metal-based catalyst.
has_exact_synonym: 1,2-hydrovinylation
has_obo_namespace: RXNO
id: RXNO:0000278

Axiom
annotated source: hydrovinylation
annotated property: definition
annotated target: The reaction of two alkenes to give an elongated alkene, employing a transition-metal-based catalyst.
database_cross_reference: rsc:db

1,4-hydrovinylation
type: Class
subclass of: hydrovinylation
definition: The reaction of a 1,3-diene with an alkene to give a 1,4-diene, usually employing a cobalt-based catalyst (see Hilt and Luers, Synthesis, 2002, 609).
has_obo_namespace: RXNO
id: RXNO:0000279

Axiom
annotated source: 1,4-hydrovinylation
annotated property: definition
annotated target: The reaction of a 1,3-diene with an alkene to give a 1,4-diene, usually employing a cobalt-based catalyst (see Hilt and Luers, Synthesis, 2002, 609).
database_cross_reference: rsc:db

alkene metathesis
type: Class
subclass of: multiple-bond metathesis
definition: A joining reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. two alkenes. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene.
has_exact_synonym: Grubbs metathesis
has_exact_synonym: Grubbs reaction
has_exact_synonym: cross metathesis
has_exact_synonym: cross-metathesis
has_exact_synonym: olefin metathesis
has_exact_synonym: transalkylidenation
has_obo_namespace: RXNO
id: RXNO:0000280

Axiom
annotated source: alkene metathesis
annotated property: definition
annotated target: A joining reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. two alkenes. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene.
database_cross_reference: rsc:db

alkyne metathesis
type: Class
subclass of: multiple-bond metathesis
definition: A joining reaction in which two carbon-carbon triple bonds are redistributed among two fragments, i.e. two alkynes. It is catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutenes). The reaction is driven by release of a low-MW alkyne.
has_obo_namespace: RXNO
id: RXNO:0000281

Axiom
annotated source: alkyne metathesis
annotated property: definition
annotated target: A joining reaction in which two carbon-carbon triple bonds are redistributed among two fragments, i.e. two alkynes. It is catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutenes). The reaction is driven by release of a low-MW alkyne.
database_cross_reference: rsc:db

enyne metathesis
type: Class
subclass of: multiple-bond metathesis
definition: A joining reaction in which a carbon-carbon double bond and a carbon-carbon triple bond are redistributed among two fragments, i.e. an alkene and an alkyne. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutenes). As a low-MW alkene is not released, the reaction is usually driven by formation of a ring.
has_obo_namespace: RXNO
id: RXNO:0000282

Axiom
annotated source: enyne metathesis
annotated property: definition
annotated target: A joining reaction in which a carbon-carbon double bond and a carbon-carbon triple bond are redistributed among two fragments, i.e. an alkene and an alkyne. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutenes). As a low-MW alkene is not released, the reaction is usually driven by formation of a ring.
database_cross_reference: rsc:db

ring-closing enyne metathesis
type: Class
subclass of: ring formation reaction step
definition: A joining reaction in which a carbon-carbon double bond and a carbon-carbon triple bond in the same molecule are redistributed to give a alkene-substituted cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by formation of the ring.
has_exact_synonym: ring closing enyne metathesis
has_obo_namespace: RXNO
id: RXNO:0000283

Axiom
annotated source: ring-closing enyne metathesis
annotated property: definition
annotated target: A joining reaction in which a carbon-carbon double bond and a carbon-carbon triple bond in the same molecule are redistributed to give a alkene-substituted cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by formation of the ring.
database_cross_reference: rsc:db

ring-opening metathesis
type: Class
subclass of: ring breaking
definition: A ring-breaking reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. an alkene and a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of ring strain in the cycloalkene.
has_exact_synonym: ring opening metathesis
has_obo_namespace: RXNO
id: RXNO:0000284

Axiom
annotated source: ring-opening metathesis
annotated property: definition
annotated target: A ring-breaking reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. an alkene and a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of ring strain in the cycloalkene.
database_cross_reference: rsc:db

Luche reaction
type: Class
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has_catalyst
  some values from: zinc atom
definition: A carbon-carbon coupling reaction where an aldehyde or ketone reacts with an allyl halide and zinc to give a homoallylic alcohol.
has_obo_namespace: RXNO
id: RXNO:0000285
comment: Not to be confused with the Luche reduction (the chemoselective reduction of an enone to an allylic alcohol).

Axiom
annotated source: Luche reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction where an aldehyde or ketone reacts with an allyl halide and zinc to give a homoallylic alcohol.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

Luche reduction
type: Class
subclass of: functional group reduction
definition: The chemoselective reduction of an enone to give an allylic alcohol, using sodium borohydride and an lanthanoid chloride, typically cerium chloride.
has_obo_namespace: RXNO
id: RXNO:0000286
comment: Not to be confused with the Luche reaction (the coupling of an aldehyde or ketone with an allyl halide).

Axiom
annotated source: Luche reduction
annotated property: definition
annotated target: The chemoselective reduction of an enone to give an allylic alcohol, using sodium borohydride and an lanthanoid chloride, typically cerium chloride.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

Lindgren oxidation
type: Class
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: The oxidation of an aldehyde to a carboxylic acid with chlorite.
has_obo_namespace: RXNO
id: RXNO:0000287

Axiom
annotated source: Lindgren oxidation
annotated property: definition
annotated target: The oxidation of an aldehyde to a carboxylic acid with chlorite.
database_cross_reference: doi:10.3891/acta.chem.scand.27-0888
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

Rosenmund-von Braun reaction
type: Class
subclass of: carbon-carbon coupling reaction
definition: A carbon-carbon coupling reaction where an aryl halide reacts with copper(I) cyanide to give an aryl nitrile.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r376/
has_exact_synonym: Rosenmund-von Braun synthesis
has_obo_namespace: RXNO
id: RXNO:0000288

Axiom
annotated source: Rosenmund-von Braun reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction where an aryl halide reacts with copper(I) cyanide to give an aryl nitrile.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

Woehler reaction
type: Class
subclass of: functional group modification
definition: The formation of urea from ammonium cyanate. Ammonium cyanate is unstable, and so is formed in situ from either (a) cyanic acid and ammonia, (b) a metal cyanate and an ammonium salt, or (c) a metal cyanate and ammonia.
has_exact_synonym: Woehler synthesis
has_exact_synonym: Wohler reaction
has_exact_synonym: Wohler synthesis
has_obo_namespace: RXNO
id: RXNO:0000289

Axiom
annotated source: Woehler reaction
annotated property: definition
annotated target: The formation of urea from ammonium cyanate. Ammonium cyanate is unstable, and so is formed in situ from either (a) cyanic acid and ammonia, (b) a metal cyanate and an ammonium salt, or (c) a metal cyanate and ammonia.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

hydrosilylation
type: Class
subclass of: addition reaction step
definition: The addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane. Addition to an aldehyde or ketone produces a silyl ether.
has_exact_synonym: hydrosilation
has_obo_namespace: RXNO
id: RXNO:0000290

Axiom
annotated source: hydrosilylation
annotated property: definition
annotated target: The addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane. Addition to an aldehyde or ketone produces a silyl ether.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

hydroamination
type: Class
subclass of: addition reaction step
definition: The addition of the N-H bond of an amine across a double bond of an alkene or alkyne, to give a more substituted amine.
has_obo_namespace: RXNO
id: RXNO:0000291

Axiom
annotated source: hydroamination
annotated property: definition
annotated target: The addition of the N-H bond of an amine across a double bond of an alkene or alkyne, to give a more substituted amine.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

hydroboration
type: Class
subclass of: addition reaction step
definition: The addition of a boron hydride across a double bond of an alkene or alkyne. The boron usually adds to the less substituted carbon.
has_obo_namespace: RXNO
id: RXNO:0000292

Axiom
annotated source: hydroboration
annotated property: definition
annotated target: The addition of a boron hydride across a double bond of an alkene or alkyne. The boron usually adds to the less substituted carbon.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

hydroboration-oxidation
type: Class
subclass of: addition reaction step
definition: The formal addition of water across a double bond of an alkene or alkyne by formation of an organoborane and in situ oxidation, typically with basic peroxide. The product is usually the less substituted alcohol.
has_obo_namespace: RXNO
id: RXNO:0000293

Axiom
annotated source: hydroboration-oxidation
annotated property: definition
annotated target: The formal addition of water across a double bond of an alkene or alkyne by formation of an organoborane and in situ oxidation, typically with basic peroxide. The product is usually the less substituted alcohol.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

hydrometallation
type: Class
subclass of: addition reaction step
definition: The reaction of any of a number of metal hydride species with an alkene or alkyne, to give an intermediate organometal species that can give various products after work-up.
has_exact_synonym: hydrometalation
has_obo_namespace: RXNO
id: RXNO:0000294

Axiom
annotated source: hydrometallation
annotated property: definition
annotated target: The reaction of any of a number of metal hydride species with an alkene or alkyne, to give an intermediate organometal species that can give various products after work-up.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

hydrozirconation
type: Class
subclass of: hydrometallation
definition: The reaction of a organozirconium hydride with an alkene or alkyne, to give an intermediate zirconium species that can give various products after work-up. The zirconium reagent used is typically Schwartz's reagent, Cp2ZrHCl.
has_obo_namespace: RXNO
id: RXNO:0000295

Axiom
annotated source: hydrozirconation
annotated property: definition
annotated target: The reaction of a organozirconium hydride with an alkene or alkyne, to give an intermediate zirconium species that can give various products after work-up. The zirconium reagent used is typically Schwartz's reagent, Cp2ZrHCl.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

hydrostannylation
type: Class
subclass of: hydrometallation
definition: The reaction of a organotin hydride with an alkene or alkyne, to give an intermediate tin species that can give various products after work-up.
has_obo_namespace: RXNO
id: RXNO:0000296

Axiom
annotated source: hydrostannylation
annotated property: definition
annotated target: The reaction of a organotin hydride with an alkene or alkyne, to give an intermediate tin species that can give various products after work-up.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

hydrotelluration
type: Class
subclass of: hydrometallation
definition: The reaction of a organotellurium hydride with an alkyne, to give a (usually (Z)-configured) vinyltellurium species.
has_obo_namespace: RXNO
id: RXNO:0000297

Axiom
annotated source: hydrotelluration
annotated property: definition
annotated target: The reaction of a organotellurium hydride with an alkyne, to give a (usually (Z)-configured) vinyltellurium species.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

Fetizon oxidation
type: Class
subclass of: functional group oxidation
definition: The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using Fetizon's reagent.
has_obo_namespace: RXNO
id: RXNO:0000298

Axiom
annotated source: Fetizon oxidation
annotated property: definition
annotated target: The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using Fetizon's reagent.
database_cross_reference: :cg
database_cross_reference: rsc:db

Vorbrueggen condensation
type: Class
subclass of: molecular skeleton joining reaction
definition: The substitution of an acylated sugar with a silylated base to give a nucleoside.
has_exact_synonym: Vorbrueggen glycosylation
has_exact_synonym: Vorbruggen condensation
has_exact_synonym: Vorbruggen glycosylation
has_obo_namespace: RXNO
id: RXNO:0000299

Axiom
annotated source: Vorbrueggen condensation
annotated property: definition
annotated target: The substitution of an acylated sugar with a silylated base to give a nucleoside.
database_cross_reference: :
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

thiol-ene reaction
type: Class
subclass of: molecular skeleton joining reaction
definition: The addition of a thiol across the double bond of an alkene to give a thioether.
has_exact_synonym: thiol-ene click reaction
has_obo_namespace: RXNO
id: RXNO:0000300

Axiom
annotated source: thiol-ene reaction
annotated property: definition
annotated target: The addition of a thiol across the double bond of an alkene to give a thioether.
database_cross_reference: :cg
database_cross_reference: rsc:db

Yamamoto polymerisation
type: Class
subclass of: polymerisation reaction
definition: The nickel-catalysed carbon-carbon coupling of a dihaloaromatic compound or aromatic bistriflate to give a polymer.
has_exact_synonym: Yamamoto coupling
has_exact_synonym: Yamamoto polymerization
has_obo_namespace: RXNO
id: RXNO:0000301

Axiom
annotated source: Yamamoto polymerisation
annotated property: definition
annotated target: The nickel-catalysed carbon-carbon coupling of a dihaloaromatic compound or aromatic bistriflate to give a polymer.
database_cross_reference: https://orcid.org/0000-0002-4077-4719
database_cross_reference: rsc:db

thermal hydrosilylation
type: Class
subclass of: hydrosilylation
definition: The thermally induced addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane, usually applied to cases where the hydrosilane is part of a silicon surface.
has_obo_namespace: RXNO
id: RXNO:0000302

Axiom
annotated source: thermal hydrosilylation
annotated property: definition
annotated target: The thermally induced addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane, usually applied to cases where the hydrosilane is part of a silicon surface.
database_cross_reference: :cg
database_cross_reference: rsc:db

photohydrosilylation
type: Class
subclass of: hydrosilylation
definition: The photochemically induced addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane, usually applied to cases where the hydrosilane is part of a silicon surface. The reaction uses UV irradiation and is usually initiated by an added photoactive compound such as a platinum catalyst.
has_exact_synonym: photo-hydrosilylation
has_obo_namespace: RXNO
id: RXNO:0000303

Axiom
annotated source: photohydrosilylation
annotated property: definition
annotated target: The photochemically induced addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane, usually applied to cases where the hydrosilane is part of a silicon surface. The reaction uses UV irradiation and is usually initiated by an added photoactive compound such as a platinum catalyst.
database_cross_reference: :cg
database_cross_reference: rsc:db

Julia-Kocienski olefination
type: Class
subclass of: olefination
subclass of: Restriction
  on property: has specified product
  some values from: olefin
definition: A carbon-carbon coupling reaction between a tetrazole sulfone and an aldehyde or ketone to give a (typically trans) alkene.
has_exact_synonym: Julia-Kocienski coupling
has_exact_synonym: Julia-Kocienski reaction
has_obo_namespace: RXNO
id: RXNO:0000304

Axiom
annotated source: Julia-Kocienski olefination
annotated property: definition
annotated target: A carbon-carbon coupling reaction between a tetrazole sulfone and an aldehyde or ketone to give a (typically trans) alkene.
database_cross_reference: rsc:db

seleno-Pummerer rearrangement
type: Class
subclass of: Pummerer rearrangement
definition: The conversion of a selenoxide with an alpha-hydrogen to an alpha-subtituted selenoether.
has_exact_synonym: selenoxide Pummerer reaction
has_obo_namespace: RXNO
id: RXNO:0000305

Axiom
annotated source: seleno-Pummerer rearrangement
annotated property: definition
annotated target: The conversion of a selenoxide with an alpha-hydrogen to an alpha-subtituted selenoether.
database_cross_reference: rsc:db

intramolecular Heck reaction
type: Class
subclass of: ring formation reaction step
subclass of: Restriction
  on property: has_catalyst
  some values from: palladium atom
definition: A carbon-carbon coupling reaction where an organohalide or triflate couples to an alkene in the same molecule, catalysed by palladium.
has_exact_synonym: intramolecular Heck-Mizoroki
has_obo_namespace: RXNO
id: RXNO:0000306

Axiom
annotated source: intramolecular Heck reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction where an organohalide or triflate couples to an alkene in the same molecule, catalysed by palladium.
database_cross_reference: rsc:db

Mori-Ban indole synthesis
type: Class
subclass of: indole synthesis
subclass of: Restriction
  on property: has specified product
  some values from: indoles
subclass of: Restriction
  on property: has specified reactant
  some values from: olefin
subclass of: Restriction
  on property: has_catalyst
  some values from: palladium atom
definition: An intramolecular Heck reaction of an ortho-halo-aniline with an alkene, catalysed by palladium.
has_exact_synonym: Mori-Ban indole reaction
has_obo_namespace: RXNO
id: RXNO:0000307

Axiom
annotated source: Mori-Ban indole synthesis
annotated property: definition
annotated target: An intramolecular Heck reaction of an ortho-halo-aniline with an alkene, catalysed by palladium.
database_cross_reference: rsc:db

Yamaguchi lactonisation
type: Class
subclass of: Yamaguchi esterification
subclass of: oxacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: lactone
definition: The intramolecular esterification of a carboxylic acid group with an alcohol group using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent) - an intramolecular Yamaguchi esterification.
has_exact_synonym: Yamaguchi lactonization
has_obo_namespace: RXNO
id: RXNO:0000308

Axiom
annotated source: Yamaguchi lactonisation
annotated property: definition
annotated target: The intramolecular esterification of a carboxylic acid group with an alcohol group using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent) - an intramolecular Yamaguchi esterification.
database_cross_reference: rsc:db

Yamaguchi esterification
type: Class
subclass of: substitution step
definition: The esterification of a carboxylic acid with an alcohol using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent).
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r479/
has_obo_namespace: RXNO
id: RXNO:0000309

Axiom
annotated source: Yamaguchi esterification
annotated property: definition
annotated target: The esterification of a carboxylic acid with an alcohol using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent).
database_cross_reference: rsc:db

oxa-Diels-Alder reaction
type: Class
subclass of: hetero-Diels-Alder reaction
definition: A Diels-Alder reaction between a diene and an aldehyde or ketone to give a six-membered oxygen-containing ring compound.
has_exact_synonym: oxa Diels-Alder cycloaddition
has_exact_synonym: oxa Diels-Alder reaction
has_exact_synonym: oxa-Diels-Alder cycloaddition
has_exact_synonym: oxo Diels-Alder cycloaddition
has_exact_synonym: oxo Diels-Alder reaction
has_exact_synonym: oxo-Diels-Alder cycloaddition
has_exact_synonym: oxo-Diels-Alder reaction
has_obo_namespace: RXNO
id: RXNO:0000310

Axiom
annotated source: oxa-Diels-Alder reaction
annotated property: definition
annotated target: A Diels-Alder reaction between a diene and an aldehyde or ketone to give a six-membered oxygen-containing ring compound.
database_cross_reference: rsc:db

Tsuji-Trost reaction
type: Class
subclass of: allylation
subclass of: carbon-carbon coupling reaction
definition: A carbon-carbon coupling reaction in which a nucleophile reacts with an allyl acetate, allyl halide, allyl carbonate, allyl carbamate, allyl phosphate, allyl sulfone or allyl nitro compound to give an allyl compound. The reaction is catalsed by Pd(0).
has_exact_synonym: Trost allylation
has_obo_namespace: RXNO
id: RXNO:0000311

Axiom
annotated source: Tsuji-Trost reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction in which a nucleophile reacts with an allyl acetate, allyl halide, allyl carbonate, allyl carbamate, allyl phosphate, allyl sulfone or allyl nitro compound to give an allyl compound. The reaction is catalsed by Pd(0).
database_cross_reference: rsc:db

Clauson-Kaas reaction
type: Class
subclass of: ring rearrangement
subclass of: pyrrole synthesis
subclass of: Restriction
  on property: has specified product
  some values from: pyrroles
definition: A ring rearrangement reaction where an amine reacts with a 2,5-dialkoxytetrahydrofuran to give a pyrrole.
has_exact_synonym: Clauson-Kaas pyrrole synthesis
has_obo_namespace: RXNO
id: RXNO:0000312

Axiom
annotated source: Clauson-Kaas reaction
annotated property: definition
annotated target: A ring rearrangement reaction where an amine reacts with a 2,5-dialkoxytetrahydrofuran to give a pyrrole.
database_cross_reference: http://www.clauson-kaas.com/cgi-files/mdmgfx/file-709-116554-7465.pdf

hetero-Diels-Alder reaction
type: Class
subclass of: Diels-Alder reaction
definition: A [4+2] cycloaddition reaction where a diene (or heterocyclic analogue) reacts with a dienophile to form an unsaturated heterocyclic six-membered ring compound.
has_obo_namespace: RXNO
id: RXNO:0000313

Axiom
annotated source: hetero-Diels-Alder reaction
annotated property: definition
annotated target: A [4+2] cycloaddition reaction where a diene (or heterocyclic analogue) reacts with a dienophile to form an unsaturated heterocyclic six-membered ring compound.
database_cross_reference: rsc:djb

RXNO_0000314
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: cycloaddition
deprecated: true

RXNO_0000315
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: condensation reaction
deprecated: true

palladium-catalysed carbon-carbon coupling reaction
type: Class
equivalent class: Class
  intersection of: carbon-carbon coupling reaction
  intersection of: Restriction
    on property: has_catalyst
    some values from: palladium atom
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has_catalyst
  some values from: palladium atom
definition: A carbon-carbon coupling reaction that is catalysed by a palladium atom.
has_obo_namespace: RXNO
id: RXNO:0000316

Axiom
annotated source: palladium-catalysed carbon-carbon coupling reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction that is catalysed by a palladium atom.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

ester condensation reaction
type: Class
equivalent class: Class
  intersection of: condensation reaction
  intersection of: Restriction
    on property: has participant beginning to exist
    some values from: carboxylic ester
subclass of: condensation reaction
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: carboxylic ester
definition: A condensation reaction that results in the production of an ester.
database_cross_reference: NAMERXN:3.6
has_obo_namespace: RXNO
id: RXNO:0000317

Axiom
annotated source: ester condensation reaction
annotated property: definition
annotated target: A condensation reaction that results in the production of an ester.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

RXNO_0000318
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: O-substitution
deprecated: true

RXNO_0000319
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: N-substitution
deprecated: true

amino group deprotection
type: Class
equivalent class: Class
  intersection of: deprotection reaction
  intersection of: Restriction
    on property: deprotects
    some values from: amino group
subclass of: deprotection reaction
subclass of: Restriction
  on property: deprotects
  some values from: amino group
definition: A deprotection reaction where the reactive centre is an amino nitrogen atom.
has_obo_namespace: RXNO
id: RXNO:0000320

Axiom
annotated source: amino group deprotection
annotated property: definition
annotated target: A deprotection reaction where the reactive centre is an amino nitrogen atom.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

amino group protection
type: Class
equivalent class: Class
  intersection of: protection reaction
  intersection of: Restriction
    on property: protects
    some values from: amino group
subclass of: protection reaction
subclass of: Restriction
  on property: protects
  some values from: amino group
definition: A protection reaction where the reactive centre is an amino nitrogen atom.
has_obo_namespace: RXNO
id: RXNO:0000321

Axiom
annotated source: amino group protection
annotated property: definition
annotated target: A protection reaction where the reactive centre is an amino nitrogen atom.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

benzylamine protection
type: Class
subclass of: amino group protection
definition: An amino group protection where the amino nitrogen atom is protected by reaction with benzylamine.
has_obo_namespace: RXNO
id: RXNO:0000322

Axiom
annotated source: benzylamine protection
annotated property: definition
annotated target: An amino group protection where the amino nitrogen atom is protected by reaction with benzylamine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

hydroxyl group protection
type: Class
equivalent class: Class
  intersection of: protection reaction
  intersection of: Restriction
    on property: protects
    some values from: hydroxy group
subclass of: protection reaction
subclass of: Restriction
  on property: protects
  some values from: hydroxy group
definition: A protection reaction where the reactive centre is a hydroxyl oxygen atom.
has_obo_namespace: RXNO
id: RXNO:0000323

Axiom
annotated source: hydroxyl group protection
annotated property: definition
annotated target: A protection reaction where the reactive centre is a hydroxyl oxygen atom.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

benzyl ether protection
type: Class
subclass of: hydroxyl group protection
subclass of: Restriction
  on property: protects
  some values from: hydroxy group
definition: A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a benzyl ether.
has_obo_namespace: RXNO
id: RXNO:0000324

Axiom
annotated source: benzyl ether protection
annotated property: definition
annotated target: A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a benzyl ether.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

carboxylic acid protection
type: Class
equivalent class: Class
  intersection of: protection reaction
  intersection of: Restriction
    on property: protects
    some values from: carboxy group
subclass of: protection reaction
subclass of: Restriction
  on property: protects
  some values from: carboxy group
definition: A protection reaction where the reactive centre is a carboxy oxygen.
has_obo_namespace: RXNO
id: RXNO:0000325

Axiom
annotated source: carboxylic acid protection
annotated property: definition
annotated target: A protection reaction where the reactive centre is a carboxy oxygen.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Boc deprotection
type: Class
subclass of: amino group deprotection
definition: An amino group deprotection reaction where a tertbutoxycarbonyl group is removed in acid conditions.
has_obo_namespace: RXNO
id: RXNO:0000326

Axiom
annotated source: Boc deprotection
annotated property: definition
annotated target: An amino group deprotection reaction where a tertbutoxycarbonyl group is removed in acid conditions.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

benzylamine deprotection
type: Class
subclass of: hydrogenation
subclass of: amino group deprotection
subclass of: Restriction
  on property: deprotects
  some values from: amino group
definition: An amino group deprotection reaction where a benzylamine group is removed by hydrogenation.
has_obo_namespace: RXNO
id: RXNO:0000327

Axiom
annotated source: benzylamine deprotection
annotated property: definition
annotated target: An amino group deprotection reaction where a benzylamine group is removed by hydrogenation.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

silyl protection
type: Class
subclass of: O-silylation
subclass of: hydroxyl group protection
definition: A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a silyl ether.
has_obo_namespace: RXNO
id: RXNO:0000328

Axiom
annotated source: silyl protection
annotated property: definition
annotated target: A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a silyl ether.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

planned synthesis
type: Class
subclass of: planned process
definition: An experimental procedure with the aim of producing a portion of a given compound or mixture.
has_obo_namespace: RXNO
id: RXNO:0000329

Axiom
annotated source: planned synthesis
annotated property: definition
annotated target: An experimental procedure with the aim of producing a portion of a given compound or mixture.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

acetate protection
type: Class
subclass of: hydroxyl group protection
definition: A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of an acetate ester.
has_exact_synonym: O-Ac protection
has_obo_namespace: RXNO
id: RXNO:0000330

Axiom
annotated source: acetate protection
annotated property: definition
annotated target: A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of an acetate ester.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

substitution step
type: Class
equivalent class: Class
  intersection of: functional modification
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: molecular substitution objective
subclass of: functional modification
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular substitution objective
definition: A functional modification step in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent.
has_obo_namespace: RXNO
id: RXNO:0000331

Axiom
annotated source: substitution step
annotated property: definition
annotated target: A functional modification step in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

aromatic substitution step
type: Class
subclass of: substitution step
subclass of: Restriction
  on property: has_part
  some values from: aromatic substitution
definition: A substitution step where one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent.
has_obo_namespace: RXNO
id: RXNO:0000332

Axiom
annotated source: aromatic substitution step
annotated property: definition
annotated target: A substitution step where one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Sandmeyer halogenation
type: Class
subclass of: Sandmeyer reaction
subclass of: Restriction
  on property: has_part
  some values from: halogenation
definition: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide to form an aromatic halide.
has_obo_namespace: RXNO
id: RXNO:0000333

Axiom
annotated source: Sandmeyer halogenation
annotated property: definition
annotated target: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide to form an aromatic halide.
database_cross_reference: RSC:db

Sandmeyer pseudohalogenation
type: Class
subclass of: Sandmeyer reaction
subclass of: Restriction
  on property: has_part
  some values from: pseudohalogenation
definition: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) pseudohalide to form an aromatic pseudohalide.
has_obo_namespace: RXNO
id: RXNO:0000334

Axiom
annotated source: Sandmeyer pseudohalogenation
annotated property: definition
annotated target: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) pseudohalide to form an aromatic pseudohalide.
database_cross_reference: RSC:db

reductive amination
type: Class
subclass of: amination
subclass of: functional group modification
definition: A functional group modification where a carbonyl oxygen is replaced by an amine.
created by: batchelorc
creation date: 2012-03-22T12:15:29Z
database_cross_reference: NAMERXN:1.2
has_obo_namespace: RXNO
id: RXNO:0000335

Axiom
annotated source: reductive amination
annotated property: definition
annotated target: A functional group modification where a carbonyl oxygen is replaced by an amine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

RXNO_0000336
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: S-substitution
deprecated: true

nitro reduction to amine
type: Class
equivalent class: Class
  intersection of: reduction
  intersection of: Restriction
    on property: has specified product
    some values from: primary amine
  intersection of: Restriction
    on property: has specified reactant
    some values from: nitro compound
subclass of: reduction
subclass of: functional group modification
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: functional group modification objective
subclass of: Restriction
  on property: has specified product
  some values from: primary amine
subclass of: Restriction
  on property: has specified reactant
  some values from: nitro compound
definition: A reduction reaction where a nitro group is reduced to an amino group.
created by: batchelorc
creation date: 2012-03-22T12:28:47Z
database_cross_reference: NAMERXN:7.1
has_obo_namespace: RXNO
id: RXNO:0000337

Axiom
annotated source: nitro reduction to amine
annotated property: definition
annotated target: A reduction reaction where a nitro group is reduced to an amino group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

amide reduction to amine
type: Class
equivalent class: Class
  intersection of: reduction
  intersection of: Restriction
    on property: has specified product
    some values from: amine
  intersection of: Restriction
    on property: has specified reactant
    some values from: amide
subclass of: reduction
subclass of: functional group modification
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: functional group modification objective
subclass of: Restriction
  on property: has specified product
  some values from: amine
subclass of: Restriction
  on property: has specified reactant
  some values from: amide
definition: A reduction process where an amide is transformed into an amine.
created by: batchelorc
creation date: 2012-03-22T12:29:51Z
database_cross_reference: NAMERXN:7.2
has_obo_namespace: RXNO
id: RXNO:0000338

Axiom
annotated source: amide reduction to amine
annotated property: definition
annotated target: A reduction process where an amide is transformed into an amine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

alkene reduction to alkane
type: Class
subclass of: hydrogenation
definition: A hydrogenation reaction where an alkene is reduced to an alkane.
created by: batchelorc
creation date: 2012-03-22T12:30:40Z
database_cross_reference: NAMERXN:7.6
has_obo_namespace: RXNO
id: RXNO:0000339

Axiom
annotated source: alkene reduction to alkane
annotated property: definition
annotated target: A hydrogenation reaction where an alkene is reduced to an alkane.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

amide N-alkylation
type: Class
subclass of: N-alkylation
definition: An N-alkylation where the reactive centre is an amide nitrogen.
created by: batchelorc
creation date: 2012-03-22T03:07:17Z
database_cross_reference: NAMERXN:1.4
has_obo_namespace: RXNO
id: RXNO:0000340

Axiom
annotated source: amide N-alkylation
annotated property: definition
annotated target: An N-alkylation where the reactive centre is an amide nitrogen.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

aniline N-alkylation
type: Class
subclass of: N-alkylation
definition: An N-alkylation where the reactive centre is an aniline nitrogen.
created by: batchelorc
creation date: 2012-03-22T03:07:44Z
database_cross_reference: NAMERXN:1.5
has_obo_namespace: RXNO
id: RXNO:0000341

Axiom
annotated source: aniline N-alkylation
annotated property: definition
annotated target: An N-alkylation where the reactive centre is an aniline nitrogen.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

nitrile reduction to amine
type: Class
subclass of: reduction
definition: A reduction where a nitrile is replaced by an amine function.
created by: batchelorc
creation date: 2012-03-22T03:12:31Z
has_obo_namespace: RXNO
id: RXNO:0000342

Axiom
annotated source: nitrile reduction to amine
annotated property: definition
annotated target: A reduction where a nitrile is replaced by an amine function.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

imine reduction to amine
type: Class
subclass of: reduction
definition: A reduction reaction where an imine function is replaced by an amine.
created by: batchelorc
creation date: 2012-03-22T03:13:12Z
has_obo_namespace: RXNO
id: RXNO:0000343

Axiom
annotated source: imine reduction to amine
annotated property: definition
annotated target: A reduction reaction where an imine function is replaced by an amine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

alkene oxidative cleavage
type: Class
subclass of: alkene oxidation
definition: An alkene oxidation where the carbon-carbon double bond is cleaved.
created by: batchelorc
creation date: 2012-03-22T03:15:25Z
database_cross_reference: NAMERXN:1.6
has_obo_namespace: RXNO
id: RXNO:0000344

Axiom
annotated source: alkene oxidative cleavage
annotated property: definition
annotated target: An alkene oxidation where the carbon-carbon double bond is cleaved.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

heteroaryl N-alkylation
type: Class
subclass of: N-alkylation
definition: An N-alkylation reaction where the reactive centre is an azacycle ring nitrogen.
created by: batchelorc
creation date: 2012-03-22T03:22:27Z
database_cross_reference: NAMERXN:1.1
has_obo_namespace: RXNO
id: RXNO:0000345

Axiom
annotated source: heteroaryl N-alkylation
annotated property: definition
annotated target: An N-alkylation reaction where the reactive centre is an azacycle ring nitrogen.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

oxacycle synthesis
type: Class
equivalent class: Class
  intersection of: molecular process
  intersection of: Restriction
    on property: has specified product
    some values from: oxacycle
subclass of: heterocycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: oxacycle
definition: A ring formation reaction where the intended product contains an oxacycle that was not in any of the reactants.
created by: batchelorc
creation date: 2012-03-22T03:24:06Z
database_cross_reference: NAMERXN:4.2
has_obo_namespace: RXNO
id: RXNO:0000346

Axiom
annotated source: oxacycle synthesis
annotated property: definition
annotated target: A ring formation reaction where the intended product contains an oxacycle that was not in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

azacycle synthesis
type: Class
equivalent class: Class
  intersection of: molecular process
  intersection of: Restriction
    on property: has specified product
    some values from: organonitrogen heterocyclic compound
subclass of: heterocycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: organonitrogen heterocyclic compound
definition: A ring formation reaction where the intended product contains an azacycle that was not in any of the reactants.
created by: batchelorc
creation date: 2012-03-22T03:24:12Z
database_cross_reference: NAMERXN:4.1
has_obo_namespace: RXNO
id: RXNO:0000347

Axiom
annotated source: azacycle synthesis
annotated property: definition
annotated target: A ring formation reaction where the intended product contains an azacycle that was not in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

thiacycle synthesis
type: Class
equivalent class: Class
  intersection of: molecular process
  intersection of: Restriction
    on property: has specified product
    some values from: organosulfur heterocyclic compound
subclass of: heterocycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: organosulfur heterocyclic compound
definition: A ring formation reaction where the intended product contains an thiacycle that was not in any of the reactants.
created by: batchelorc
creation date: 2012-03-22T03:24:23Z
database_cross_reference: NAMERXN:4.3
has_obo_namespace: RXNO
id: RXNO:0000348

Axiom
annotated source: thiacycle synthesis
annotated property: definition
annotated target: A ring formation reaction where the intended product contains an thiacycle that was not in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

heterocycle synthesis
type: Class
equivalent class: Class
  intersection of: molecular process
  intersection of: Restriction
    on property: has specified product
    some values from: heterocyclic compound
subclass of: ring formation reaction step
subclass of: Restriction
  on property: has specified product
  some values from: heterocyclic compound
definition: A ring formation reaction where the intended product contains a heterocycle that was not in any of the reactants.
created by: batchelorc
creation date: 2012-03-22T03:24:34Z
database_cross_reference: NAMERXN:4
has_obo_namespace: RXNO
id: RXNO:0000349

Axiom
annotated source: heterocycle synthesis
annotated property: definition
annotated target: A ring formation reaction where the intended product contains a heterocycle that was not in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

alkyne reduction to alkane
type: Class
subclass of: hydrogenation
definition: A hydrogenation reaction where an alkyne is reduced to an alkane.
created by: batchelorc
creation date: 2012-03-22T03:30:01Z
database_cross_reference: NAMERXN:7.7
has_obo_namespace: RXNO
id: RXNO:0000350

Axiom
annotated source: alkyne reduction to alkane
annotated property: definition
annotated target: A hydrogenation reaction where an alkyne is reduced to an alkane.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

aryl reduction to cycloalkyl
type: Class
subclass of: hydrogenation
definition: A hydrogenation reaction where an aryl ring is reduced to a cycloalkyl ring.
created by: batchelorc
creation date: 2012-03-22T03:30:50Z
has_obo_namespace: RXNO
id: RXNO:0000351

Axiom
annotated source: aryl reduction to cycloalkyl
annotated property: definition
annotated target: A hydrogenation reaction where an aryl ring is reduced to a cycloalkyl ring.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

heteroaryl reduction to saturated heterocycle
type: Class
subclass of: hydrogenation
definition: A hydrogenation reaction where a heteroaryl is reduced to a saturated heterocycle.
created by: batchelorc
creation date: 2012-03-22T03:31:49Z
has_obo_namespace: RXNO
id: RXNO:0000352

Axiom
annotated source: heteroaryl reduction to saturated heterocycle
annotated property: definition
annotated target: A hydrogenation reaction where a heteroaryl is reduced to a saturated heterocycle.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

alcohol oxidation to carboxylic acid
type: Class
subclass of: alcohol oxidation
definition: An alcohol oxidation where the alcohol centre is replaced with a carboxy group.
created by: batchelorc
creation date: 2012-03-22T03:34:20Z
has_obo_namespace: RXNO
id: RXNO:0000353

Axiom
annotated source: alcohol oxidation to carboxylic acid
annotated property: definition
annotated target: An alcohol oxidation where the alcohol centre is replaced with a carboxy group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

benzylic oxidation
type: Class
subclass of: oxidation
definition: An oxidation reaction where a carbon centre bonded to the benzene ring is oxidized to a carboxyl group.
created by: batchelorc
creation date: 2012-03-22T03:37:52Z
has_obo_namespace: RXNO
id: RXNO:0000354

Axiom
annotated source: benzylic oxidation
annotated property: definition
annotated target: An oxidation reaction where a carbon centre bonded to the benzene ring is oxidized to a carboxyl group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

allylic oxidation
type: Class
subclass of: oxidation
definition: An oxidation reaction where an allylic C-H bond is replaced by a C=O bond.
created by: batchelorc
creation date: 2012-03-22T03:39:47Z
has_obo_namespace: RXNO
id: RXNO:0000355
comment: This can be done with, for instance, selenium dioxide.

Axiom
annotated source: allylic oxidation
annotated property: definition
annotated target: An oxidation reaction where an allylic C-H bond is replaced by a C=O bond.
database_cross_reference: http://www.chemtube3d.com/ox_se_allylic.html
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Jones oxidation
type: Class
subclass of: alcohol oxidation
subclass of: functional group oxidation
definition: An oxidation reaction where an alcohol is oxidized to the corresponding carbonyl compound by a dichromate ion.
created by: batchelorc
creation date: 2012-03-22T03:39:47Z
has_obo_namespace: RXNO
id: RXNO:0000356

Axiom
annotated source: Jones oxidation
annotated property: definition
annotated target: An oxidation reaction where an alcohol is oxidized to the corresponding carbonyl compound by a dichromate ion.
database_cross_reference: http://www.chemtube3d.com/ox_jones_oxidation.html
database_cross_reference: https://orcid.org/0000-0001-5985-7429

N-acylation to amide
type: Class
subclass of: N-acylation
definition: An acylation reaction where a nitrogen atom is acylated to form an amide.
created by: batchelorc
creation date: 2012-03-22T03:39:47Z
database_cross_reference: NAMERXN:2.1
has_obo_namespace: RXNO
id: RXNO:0000357

Axiom
annotated source: N-acylation to amide
annotated property: definition
annotated target: An acylation reaction where a nitrogen atom is acylated to form an amide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

N-acylation to urea
type: Class
subclass of: N-acylation
definition: An acylation reaction where a nitrogen atom is acylated to form a urea.
created by: batchelorc
creation date: 2012-03-22T03:39:47Z
database_cross_reference: NAMERXN:2.3
has_obo_namespace: RXNO
id: RXNO:0000358

Axiom
annotated source: N-acylation to urea
annotated property: definition
annotated target: An acylation reaction where a nitrogen atom is acylated to form a urea.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

N-acylation to carbamate
type: Class
subclass of: N-acylation
definition: An N-acylation reaction where a nitrogen centre is acylated to form a carbamate.
created by: batchelorc
creation date: 2012-03-22T04:09:47Z
database_cross_reference: NAMERXN:2.4
has_obo_namespace: RXNO
id: RXNO:0000359

Axiom
annotated source: N-acylation to carbamate
annotated property: definition
annotated target: An N-acylation reaction where a nitrogen centre is acylated to form a carbamate.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

O-acylation to ester
type: Class
subclass of: O-acylation
definition: An O-acylation reaction where an oxygen centre is acylated to result in an ester.
created by: batchelorc
creation date: 2012-03-22T04:10:47Z
database_cross_reference: NAMERXN:2.6
has_obo_namespace: RXNO
id: RXNO:0000360

Axiom
annotated source: O-acylation to ester
annotated property: definition
annotated target: An O-acylation reaction where an oxygen centre is acylated to result in an ester.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Pinner reaction
type: Class
subclass of: functional group modification
subclass of: Restriction
  on property: has_part
  some values from: nitrile alcoholysis
definition: A functional group modification where a nitrile reacts with an alcohol under acid catalysis to form an amidine or ester.
has_obo_namespace: RXNO
id: RXNO:0000361

Axiom
annotated source: Pinner reaction
annotated property: definition
annotated target: A functional group modification where a nitrile reacts with an alcohol under acid catalysis to form an amidine or ester.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

nitrile alcoholysis
type: Class
subclass of: oxidation
definition: An oxidation reaction where a nitrile reacts with an alcohol to form an alkyl imidate.
has_obo_namespace: RXNO
id: RXNO:0000362

Axiom
annotated source: nitrile alcoholysis
annotated property: definition
annotated target: An oxidation reaction where a nitrile reacts with an alcohol to form an alkyl imidate.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

amide to imidoyl chloride conversion
type: Class
subclass of: functional group modification
subclass of: Restriction
  on property: has specified reactant
  some values from: amide
definition: A functional group modification where an amide is converted to an imidoyl chloride.
created by: batchelorc
creation date: 2012-03-22T05:04:20Z
database_cross_reference: NAMERXN:9.2
has_obo_namespace: RXNO
id: RXNO:0000363

Axiom
annotated source: amide to imidoyl chloride conversion
annotated property: definition
annotated target: A functional group modification where an amide is converted to an imidoyl chloride.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

alcohol to halide conversion
type: Class
subclass of: functional group modification
definition: A functional group modification where an alcohol is converted to a halide.
created by: batchelorc
creation date: 2012-03-22T05:05:15Z
database_cross_reference: NAMERXN:9.1
has_obo_namespace: RXNO
id: RXNO:0000364

Axiom
annotated source: alcohol to halide conversion
annotated property: definition
annotated target: A functional group modification where an alcohol is converted to a halide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

carboxylic acid to acid chloride conversion
type: Class
subclass of: functional group modification
definition: A functional group modification where a carboxylic acid is converted to an acid chloride.
created by: batchelorc
creation date: 2012-03-22T05:06:09Z
database_cross_reference: NAMERXN:9.3
has_obo_namespace: RXNO
id: RXNO:0000365

Axiom
annotated source: carboxylic acid to acid chloride conversion
annotated property: definition
annotated target: A functional group modification where a carboxylic acid is converted to an acid chloride.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

nitrile to acid conversion
type: Class
subclass of: functional group modification
definition: A functional group modification where a nitrile is transformed into a carboxylic acid.
created by: batchelorc
creation date: 2012-03-22T05:12:32Z
database_cross_reference: NAMERXN:9.4
has_obo_namespace: RXNO
id: RXNO:0000366

Axiom
annotated source: nitrile to acid conversion
annotated property: definition
annotated target: A functional group modification where a nitrile is transformed into a carboxylic acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

carbonyl compound to imine conversion
type: Class
subclass of: functional group modification
definition: A functional group modification where a carbonyl compound is converted to an imine.
created by: batchelorc
creation date: 2012-03-22T05:17:03Z
database_cross_reference: NAMERXN:9.6
has_obo_namespace: RXNO
id: RXNO:0000367

Axiom
annotated source: carbonyl compound to imine conversion
annotated property: definition
annotated target: A functional group modification where a carbonyl compound is converted to an imine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Crabbé homologation
type: Class
subclass of: alkene oxidation
subclass of: chain lengthening
subclass of: Restriction
  on property: has_participant
  some values from: amine
subclass of: Restriction
  on property: has specified product
  some values from: allenes
subclass of: Restriction
  on property: has specified reactant
  some values from: formaldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: alkene
definition: Oxidation of an alkene to an allene by heating with formaldehyde, an amine and an inorganic salt.
created by: batchelorc
creation date: 2014-01-08T13:48:00Z
has_exact_synonym: Crabbe homologation
has_obo_namespace: RXNO
id: RXNO:0000368

Axiom
annotated source: Crabbé homologation
annotated property: definition
annotated target: Oxidation of an alkene to an allene by heating with formaldehyde, an amine and an inorganic salt.
database_cross_reference: doi:10.1039/c39790000859
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Friedel-Crafts reaction
type: Class
equivalent class: Class
  union of: Friedel-Crafts acylation
  union of: Friedel-Crafts alkylation
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: arene
definition: A carbon-carbon coupling reaction between an arene and a carbonyl compound (an acylation) or an alkyl compound that can form a carbocation (an alkylation) to form a substituted arene.
database_cross_reference: NAMERXN:3.10
has_obo_namespace: RXNO
id: RXNO:0000369

Axiom
annotated source: Friedel-Crafts reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction between an arene and a carbonyl compound (an acylation) or an alkyl compound that can form a carbocation (an alkylation) to form a substituted arene.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Demko-Sharpless reaction
type: Class
subclass of: functional group modification
subclass of: Restriction
  on property: has specified product
  some values from: tetrazoles
subclass of: Restriction
  on property: has specified reactant
  some values from: nitrile
subclass of: Restriction
  on property: has specified reactant
  some values from: sodium azide
definition: A functional group modification of a nitrile to a 1H-tetrazole by addition of sodium azide.
has_obo_namespace: RXNO
id: RXNO:0000370

Axiom
annotated source: Demko-Sharpless reaction
annotated property: definition
annotated target: A functional group modification of a nitrile to a 1H-tetrazole by addition of sodium azide.
database_cross_reference: doi:10.1021/jo010635w
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Griess reaction
type: Class
subclass of: diazotisation
definition: A diazotisation that proceeds by the addition of nitrous acid, nitric acid and water, resulting in a diazonium nitrate salt.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r174/
has_obo_namespace: RXNO
id: RXNO:0000371

Axiom
annotated source: Griess reaction
annotated property: definition
annotated target: A diazotisation that proceeds by the addition of nitrous acid, nitric acid and water, resulting in a diazonium nitrate salt.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

heteroaryl N-arylation
type: Class
subclass of: N-arylation
definition: An N-arylation reaction where the reactive centre is an azacycle ring nitrogen.
database_cross_reference: NAMERXN:1.3
has_obo_namespace: RXNO
id: RXNO:0000372

Axiom
annotated source: heteroaryl N-arylation
annotated property: definition
annotated target: An N-arylation reaction where the reactive centre is an azacycle ring nitrogen.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

functional group addition step
type: Class
equivalent class: Class
  intersection of: functional modification
  intersection of: Restriction
    on property: achieves_planned_objective
    some values from: functional group addition objective
subclass of: formation of covalent bond with group
subclass of: functional modification
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: functional group addition objective
definition: A planned reaction step in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged.
database_cross_reference: NAMERXN:10
has_obo_namespace: RXNO
id: RXNO:0000373
comment: this is not part of David's grand diagram - well spotted Roger

Axiom
annotated source: functional group addition step
annotated property: definition
annotated target: A planned reaction step in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Chan-Lam coupling
type: Class
subclass of: arylation
subclass of: functional group oxidation
definition: Arylation of an amine or an alcohol with an arylboronic acid, stannane or siloxane in air with a copper acetate catalyst.
has_exact_synonym: Chan-Lam reaction
has_exact_synonym: Chan-Lam-Evans coupling
has_exact_synonym: Chan-Lam-Evans reaction
has_obo_namespace: RXNO
id: RXNO:0000374
comment: The canonical variant is the N-arylation of an amine with an arylboronic acid.

Axiom
annotated source: Chan-Lam coupling
annotated property: definition
annotated target: Arylation of an amine or an alcohol with an arylboronic acid, stannane or siloxane in air with a copper acetate catalyst.
database_cross_reference: doi:10.1016/j.tet.2012.06.015

RXNO_0000375
type: Class
IAO_0000231: IAO_0000227
IAO_0100001: Menshutkin reaction
deprecated: true

Eschweiler-Clarke methylation
type: Class
subclass of: N-methylation
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified product
  some values from: tertiary amine
subclass of: Restriction
  on property: has specified reactant
  some values from: formaldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: amine
definition: N-methylation of a primary or secondary amine with formic acid and formaldehyde to yield a tertiary amine.
has_exact_synonym: Eschweiler-Clarke reaction
has_obo_namespace: RXNO
id: RXNO:0000376

Axiom
annotated source: Eschweiler-Clarke methylation
annotated property: definition
annotated target: N-methylation of a primary or secondary amine with formic acid and formaldehyde to yield a tertiary amine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Scholl reaction
type: Class
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has_part
  some values from: Lewis acid catalysis
definition: Coupling of two aromatic rings in the presence of a Lewis acid catalyst.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r390/
has_obo_namespace: RXNO
id: RXNO:0000377

Axiom
annotated source: Scholl reaction
annotated property: definition
annotated target: Coupling of two aromatic rings in the presence of a Lewis acid catalyst.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

intramolecular Scholl reaction
type: Class
subclass of: molecular skeleton joining reaction
subclass of: ring formation reaction step
subclass of: Scholl reaction
definition: Scholl reaction within a single molecule to form a larger ring system.
has_obo_namespace: RXNO
id: RXNO:0000378

Axiom
annotated source: intramolecular Scholl reaction
annotated property: definition
annotated target: Scholl reaction within a single molecule to form a larger ring system.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

intermolecular Scholl reaction
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Scholl reaction
definition: Scholl reaction between two aromatic molecules to form a single molecule.
has_obo_namespace: RXNO
id: RXNO:0000379

Axiom
annotated source: intermolecular Scholl reaction
annotated property: definition
annotated target: Scholl reaction between two aromatic molecules to form a single molecule.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Robinson annulation
type: Class
subclass of: fused-ring-system formation
subclass of: Restriction
  on property: has_part
  some values from: cyclization
subclass of: Restriction
  on property: has_part
  some values from: Michael addition
subclass of: Restriction
  on property: has_part
  some values from: aldol condensation
definition: Reaction of a cyclohexanone with methyl vinyl ketone to form a fused-ring cyclohexenone. It is a Michael reaction followed by an intramolecular aldol condensation.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r373/
has_obo_namespace: RXNO
id: RXNO:0000380

Axiom
annotated source: Robinson annulation
annotated property: definition
annotated target: Reaction of a cyclohexanone with methyl vinyl ketone to form a fused-ring cyclohexenone. It is a Michael reaction followed by an intramolecular aldol condensation.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Tiffeneau-Demjanov rearrangement
type: Class
subclass of: rearrangement step
definition: Rearrangement of a beta-amino alcohol to yield a carbonyl compound. In the first step the amine is diazotised by reaction with nitrous acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r432/
has_obo_namespace: RXNO
id: RXNO:0000381

Axiom
annotated source: Tiffeneau-Demjanov rearrangement
annotated property: definition
annotated target: Rearrangement of a beta-amino alcohol to yield a carbonyl compound. In the first step the amine is diazotised by reaction with nitrous acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Demjanov rearrangement
type: Class
subclass of: rearrangement step
subclass of: substitution step
definition: Substitution reaction of a primary amine via deazotisation to yield a mixture of the corresponding primary alcohol and secondary alcohol.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r106/
has_obo_namespace: RXNO
id: RXNO:0000382
comment: TODO: Not *entirely* sure how we classify this. Have given it multiple parentage for the now.

Axiom
annotated source: Demjanov rearrangement
annotated property: definition
annotated target: Substitution reaction of a primary amine via deazotisation to yield a mixture of the corresponding primary alcohol and secondary alcohol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

thiol-yne reaction
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified product
  some values from: organic sulfide
subclass of: Restriction
  on property: has specified reactant
  some values from: alkyne
subclass of: Restriction
  on property: has specified reactant
  some values from: thiol
subclass of: Restriction
  on property: has_intermediate
  some values from: sulfanyl
definition: Reaction of an thiol with an alkyne to form an alkenyl sulfide.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-05-05T09:08:42Z
has_exact_synonym: alkyne hydrothiolation
has_obo_namespace: RXNO
id: RXNO:0000383

Axiom
annotated source: thiol-yne reaction
annotated property: definition
annotated target: Reaction of an thiol with an alkyne to form an alkenyl sulfide.
database_cross_reference: https://en.wikipedia.org/wiki/Thiol-yne_reaction

cyclic alpha-haloketone Favorskii rearrangement
type: Class
subclass of: ring contraction
subclass of: Favorskii rearrangement
definition: Base-catalysed rearrangement of a cyclic alpha-haloketone to the ring-contracted cyclic carboxylic acid.
has_obo_namespace: RXNO
id: RXNO:0000384

Axiom
annotated source: cyclic alpha-haloketone Favorskii rearrangement
annotated property: definition
annotated target: Base-catalysed rearrangement of a cyclic alpha-haloketone to the ring-contracted cyclic carboxylic acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Favorskii rearrangement
type: Class
subclass of: rearrangement step
definition: Base-catalysed rearrangement of an alpha-haloketone to a carboxylic acid or ester or amide.
has_obo_namespace: RXNO
id: RXNO:0000385

Axiom
annotated source: Favorskii rearrangement
annotated property: definition
annotated target: Base-catalysed rearrangement of an alpha-haloketone to a carboxylic acid or ester or amide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Wallach degradation
type: Class
subclass of: ring contraction
subclass of: Restriction
  on property: has_part
  some values from: decarboxylation
subclass of: Restriction
  on property: has_part
  some values from: cyclic alpha-haloketone Favorskii rearrangement
definition: Favorskii rearrangement of a cyclic alpha-dibromoketone followed by decarboxylation to yield a ring-contracted cyclic ketone.
has_obo_namespace: RXNO
id: RXNO:0000386

Axiom
annotated source: Wallach degradation
annotated property: definition
annotated target: Favorskii rearrangement of a cyclic alpha-dibromoketone followed by decarboxylation to yield a ring-contracted cyclic ketone.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Seyferth-Gilbert homologation
type: Class
subclass of: carbonyl oxidation to alkyne
definition: Reaction of a carbonyl compound with a dimethyl diazomethyl phosphonate under basic conditions to yield an alkyne.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r395/
has_obo_namespace: RXNO
id: RXNO:0000387

Axiom
annotated source: Seyferth-Gilbert homologation
annotated property: definition
annotated target: Reaction of a carbonyl compound with a dimethyl diazomethyl phosphonate under basic conditions to yield an alkyne.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Seyferth-Gilbert aldehyde homologation
type: Class
subclass of: chain lengthening
subclass of: Seyferth-Gilbert homologation
subclass of: Restriction
  on property: has specified product
  some values from: terminal acetylenic compound
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: Reaction of an aldehyde with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne.
has_obo_namespace: RXNO
id: RXNO:0000388

Axiom
annotated source: Seyferth-Gilbert aldehyde homologation
annotated property: definition
annotated target: Reaction of an aldehyde with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Seyferth-Gilbert ketone homologation
type: Class
subclass of: molecular skeleton insertion reaction
subclass of: Seyferth-Gilbert homologation
subclass of: Restriction
  on property: has specified product
  some values from: terminal acetylenic compound
definition: Reaction of a ketone with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne.
has_obo_namespace: RXNO
id: RXNO:0000389

Axiom
annotated source: Seyferth-Gilbert ketone homologation
annotated property: definition
annotated target: Reaction of a ketone with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Seyferth-Gilbert-Bestmann homologation
type: Class
subclass of: Seyferth-Gilbert aldehyde homologation
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
definition: Seyferth-Gilbert aldehyde homologation where the Seyferth-Gilbert reagent is generated in situ by reaction with methanol and potassium carbonate.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r395/
has_exact_synonym: Bestmann modification
has_exact_synonym: Ohira-Bestmann homologation
has_exact_synonym: Ohira-Bestmann modification
has_obo_namespace: RXNO
id: RXNO:0000390

Axiom
annotated source: Seyferth-Gilbert-Bestmann homologation
annotated property: definition
annotated target: Seyferth-Gilbert aldehyde homologation where the Seyferth-Gilbert reagent is generated in situ by reaction with methanol and potassium carbonate.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Knorr pyrazole synthesis
type: Class
subclass of: molecular dehydration reaction
subclass of: pyrazole synthesis
definition: Synthesis of a pyrazole by condensation of a 1,3-dicarbonyl compound with a hydrazine, hydrazide, semicarbazide or aminoguanidine.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r233/
has_obo_namespace: RXNO
id: RXNO:0000391

Axiom
annotated source: Knorr pyrazole synthesis
annotated property: definition
annotated target: Synthesis of a pyrazole by condensation of a 1,3-dicarbonyl compound with a hydrazine, hydrazide, semicarbazide or aminoguanidine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

pyrazole synthesis
type: Class
equivalent class: Class
  intersection of: azacycle synthesis
  intersection of: Restriction
    on property: has specified product
    some values from: pyrazoles
subclass of: azacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: pyrazoles
definition: A reaction in which the intended product is a pyrazole that was not present in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000392

Axiom
annotated source: pyrazole synthesis
annotated property: definition
annotated target: A reaction in which the intended product is a pyrazole that was not present in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

quinoline synthesis
type: Class
equivalent class: Class
  intersection of: molecular process
  intersection of: Restriction
    on property: has specified product
    some values from: quinolines
subclass of: fused-ring-system formation
subclass of: azacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: quinolines
definition: A reaction in which the intended product is a quinoline that was not present in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000393

Axiom
annotated source: quinoline synthesis
annotated property: definition
annotated target: A reaction in which the intended product is a quinoline that was not present in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Knorr quinoline synthesis
type: Class
subclass of: quinoline synthesis
subclass of: Restriction
  on property: has_part
  some values from: molecular dehydration reaction
definition: Synthesis of an alpha-hydroxyquinoline by reaction of a beta-ketoester and an arylamine then dehydration with concentrated sulfuric acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r234/
has_obo_namespace: RXNO
id: RXNO:0000394

Axiom
annotated source: Knorr quinoline synthesis
annotated property: definition
annotated target: Synthesis of an alpha-hydroxyquinoline by reaction of a beta-ketoester and an arylamine then dehydration with concentrated sulfuric acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

indole synthesis
type: Class
equivalent class: Class
  intersection of: molecular process
  intersection of: Restriction
    on property: has specified product
    some values from: indoles
subclass of: fused-ring-system formation
subclass of: azacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: indoles
definition: A reaction in which the intended product is an indole that was not present in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000395

Axiom
annotated source: indole synthesis
annotated property: definition
annotated target: A reaction in which the intended product is an indole that was not present in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Larock indole synthesis
type: Class
subclass of: indole synthesis
subclass of: Restriction
  on property: has_catalyst
  some values from: palladium atom
definition: Palladium-catalysed synthesis of a 2,3-substituted indole by reaction of an ortho-iodoaniline with an internal alkyne.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r250/
has_exact_synonym: Larock indolisation
has_exact_synonym: Larock indolization
has_obo_namespace: RXNO
id: RXNO:0000396

Axiom
annotated source: Larock indole synthesis
annotated property: definition
annotated target: Palladium-catalysed synthesis of a 2,3-substituted indole by reaction of an ortho-iodoaniline with an internal alkyne.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Pechmann pyrazole synthesis
type: Class
subclass of: pyrazole synthesis
definition: Reaction of an organic diazo compound with an acetylene to yield a pyrazole.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r323/
has_obo_namespace: RXNO
id: RXNO:0000397

Axiom
annotated source: Pechmann pyrazole synthesis
annotated property: definition
annotated target: Reaction of an organic diazo compound with an acetylene to yield a pyrazole.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

benzimidazole synthesis
type: Class
subclass of: fused-ring-system formation
subclass of: Restriction
  on property: has specified product
  some values from: benzimidazoles
definition: A reaction in which the intended product is a benzimidazole that was not present in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000398

Axiom
annotated source: benzimidazole synthesis
annotated property: definition
annotated target: A reaction in which the intended product is a benzimidazole that was not present in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Phillips benzimidazole synthesis
type: Class
subclass of: benzimidazole synthesis
definition: Reaction of an ortho-diaminobenzene with a carboxylic acid under heat to yield a benzimidazole.
has_exact_synonym: Phillips benzimidazole condensation
has_obo_namespace: RXNO
id: RXNO:0000399
comment: This may be done in the presence of an acid, hexamethyldisilazane in the presence of catalytic triflic acid, a titanium catalyst, elevated pressure, or under UV. [ISBN:9780080534459]

Axiom
annotated source: Phillips benzimidazole synthesis
annotated property: definition
annotated target: Reaction of an ortho-diaminobenzene with a carboxylic acid under heat to yield a benzimidazole.
database_cross_reference: ISBN:9780080534459
database_cross_reference: https://orcid.org/0000-0001-5985-7429

pyrimidine synthesis
type: Class
subclass of: azacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: pyrimidines
definition: A reaction in which the intended product is a pyrimidine that was not present in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000400

Axiom
annotated source: pyrimidine synthesis
annotated property: definition
annotated target: A reaction in which the intended product is a pyrimidine that was not present in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

triazine synthesis
type: Class
subclass of: azacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: triazines
definition: A reaction in which the intended product is a triazine that was not present in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000401

Axiom
annotated source: triazine synthesis
annotated property: definition
annotated target: A reaction in which the intended product is a triazine that was not present in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Pinner pyrimidine synthesis
type: Class
subclass of: pyrimidine synthesis
subclass of: Restriction
  on property: has_part
  some values from: molecular dehydration reaction
definition: Reaction of a 1,3-dicarbonyl compound with an amidine to yield a pyrimidine.
has_obo_namespace: RXNO
id: RXNO:0000402

Axiom
annotated source: Pinner pyrimidine synthesis
annotated property: definition
annotated target: Reaction of a 1,3-dicarbonyl compound with an amidine to yield a pyrimidine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Pinner triazine synthesis
type: Class
subclass of: triazine synthesis
definition: Reaction of aryl amidines or halogenated aliphatics amidines with phosgene to yield a 2-hydroxy-4,6-diaryl-s-triazine with loss of ammonia.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r343/
has_obo_namespace: RXNO
id: RXNO:0000403

Axiom
annotated source: Pinner triazine synthesis
annotated property: definition
annotated target: Reaction of aryl amidines or halogenated aliphatics amidines with phosgene to yield a 2-hydroxy-4,6-diaryl-s-triazine with loss of ammonia.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

oxa-Pictet-Spengler reaction
type: Class
subclass of: condensation reaction
subclass of: fused-ring-system formation
subclass of: oxacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: oxacycle
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: Cyclisation-condensation of a beta-arylethanol with an aldehyde to yield an ortho,peri-fused aryl-oxacycle.
has_obo_namespace: RXNO
id: RXNO:0000404

Axiom
annotated source: oxa-Pictet-Spengler reaction
annotated property: definition
annotated target: Cyclisation-condensation of a beta-arylethanol with an aldehyde to yield an ortho,peri-fused aryl-oxacycle.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Prilezhaev epoxidation
type: Class
subclass of: epoxidation
subclass of: oxacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: epoxide
definition: Epoxidation of an alkene by reaction with a peroxy acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r351/
has_exact_synonym: Prileschajew reaction
has_exact_synonym: Prilezhaev reaction
has_obo_namespace: RXNO
id: RXNO:0000405

Axiom
annotated source: Prilezhaev epoxidation
annotated property: definition
annotated target: Epoxidation of an alkene by reaction with a peroxy acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Appel halogenation
type: Class
subclass of: alcohol to halide conversion
subclass of: Restriction
  on property: has specified product
  some values from: haloalkane
subclass of: Restriction
  on property: has specified reactant
  some values from: alcohol
subclass of: Restriction
  on property: has specified reactant
  some values from: triphenylphosphane oxide
definition: Conversion of an alcohol to an alkyl halide with triphenylphosphine and a halide source.
has_exact_synonym: Appel reaction
has_obo_namespace: RXNO
id: RXNO:0000406

Axiom
annotated source: Appel halogenation
annotated property: definition
annotated target: Conversion of an alcohol to an alkyl halide with triphenylphosphine and a halide source.
database_cross_reference: doi:10.1002/anie.197508011
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Appel iodination
type: Class
subclass of: Appel halogenation
subclass of: Restriction
  on property: has specified product
  some values from: iodoalkane
definition: Conversion of an alcohol to an alkyl iodide with triphenylphosphine and tetraiodomethane.
has_obo_namespace: RXNO
id: RXNO:0000407

Axiom
annotated source: Appel iodination
annotated property: definition
annotated target: Conversion of an alcohol to an alkyl iodide with triphenylphosphine and tetraiodomethane.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Appel chlorination
type: Class
subclass of: Appel halogenation
subclass of: Restriction
  on property: has specified product
  some values from: chloroalkane
subclass of: Restriction
  on property: has specified reactant
  some values from: tetrachloromethane
definition: Conversion of an alcohol to an alkyl chloride with triphenylphosphine and tetrachloromethane.
has_obo_namespace: RXNO
id: RXNO:0000408

Axiom
annotated source: Appel chlorination
annotated property: definition
annotated target: Conversion of an alcohol to an alkyl chloride with triphenylphosphine and tetrachloromethane.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Appel bromination
type: Class
equivalent class: Class
  union of: Appel bromination with tetrabromomethane
  union of: Appel bromination with bromine
subclass of: Appel halogenation
subclass of: Restriction
  on property: has specified product
  some values from: bromoalkane
definition: Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane or bromine.
has_obo_namespace: RXNO
id: RXNO:0000409

Axiom
annotated source: Appel bromination
annotated property: definition
annotated target: Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane or bromine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Hofmann rearrangement
type: Class
subclass of: end-of-chain chain shortening
definition: Rearrangement of a primary carboxylic amide to an isocyanate.
has_obo_namespace: RXNO
id: RXNO:0000410
comment: This counts as an end-of-chain chain shortening because the terminal carbon is separated from the skeleton into the isocyanate group.

Axiom
annotated source: Hofmann rearrangement
annotated property: definition
annotated target: Rearrangement of a primary carboxylic amide to an isocyanate.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Hofmann reaction
type: Class
subclass of: end-of-chain chain shortening
subclass of: Restriction
  on property: has_part
  some values from: Hofmann rearrangement
definition: Conversion of a primary carboxylic amide to the lower homologue primary amine. The first step is the Hofmann rearrangement
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r209/
has_obo_namespace: RXNO
has_related_synonym: Hofmann degradation
id: RXNO:0000411

Axiom
annotated source: Hofmann reaction
annotated property: definition
annotated target: Conversion of a primary carboxylic amide to the lower homologue primary amine. The first step is the Hofmann rearrangement
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Newman-Kwart rearrangement
type: Class
subclass of: functional group modification
definition: Rearrangement of an O-aryl thiocarbamate to an S-aryl thiocarbamate by migration of the aryl group.
database_cross_reference: https://www.wikidata.org/wiki/Q909753
has_obo_namespace: RXNO
id: RXNO:0000412

Axiom
annotated source: Newman-Kwart rearrangement
annotated property: definition
annotated target: Rearrangement of an O-aryl thiocarbamate to an S-aryl thiocarbamate by migration of the aryl group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Zincke nitration
type: Class
subclass of: nitration
subclass of: aromatic substitution step
definition: Substitution of phenol ortho- or para-bromo or iodo groups by a nitro group on treatment with nitrous acid or a nitrite in acetic acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r484/
database_cross_reference: https://www.wikidata.org/wiki/Q1061336
has_obo_namespace: RXNO
id: RXNO:0000413

Axiom
annotated source: Zincke nitration
annotated property: definition
annotated target: Substitution of phenol ortho- or para-bromo or iodo groups by a nitro group on treatment with nitrous acid or a nitrite in acetic acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r484/

haloethanoate ester-aldehyde Darzens reaction
type: Class
subclass of: chain lengthening
subclass of: Darzens reaction
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: A coupling of an aldehyde with an alpha-haloethanoate ester to form the next homologous aldehyde.
has_obo_namespace: RXNO
id: RXNO:0000414
comment: These are not necessary-and-sufficient conditions because we can't say "one longer" in OWL.

Axiom
annotated source: haloethanoate ester-aldehyde Darzens reaction
annotated property: definition
annotated target: A coupling of an aldehyde with an alpha-haloethanoate ester to form the next homologous aldehyde.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

haloethanoate ester-ketone Darzens reaction
type: Class
subclass of: Darzens reaction
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: ketone
definition: A coupling of a ketone with an alpha-haloethanoate ester to replace the oxo group with a formyl group.
has_obo_namespace: RXNO
id: RXNO:0000415

Axiom
annotated source: haloethanoate ester-ketone Darzens reaction
annotated property: definition
annotated target: A coupling of a ketone with an alpha-haloethanoate ester to replace the oxo group with a formyl group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

phthalimide protection
type: Class
subclass of: amino group protection
subclass of: Restriction
  on property: protects
  some values from: amino group
subclass of: Restriction
  on property: has specified reactant
  some values from: phthalic anhydride
definition: Protection of a primary amino group by reaction with phthalic anhydride.
has_obo_namespace: RXNO
id: RXNO:0000418

Axiom
annotated source: phthalimide protection
annotated property: definition
annotated target: Protection of a primary amino group by reaction with phthalic anhydride.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

phthalimide deprotection
type: Class
subclass of: amino group deprotection
subclass of: Restriction
  on property: deprotects
  some values from: amino group
definition: Conversion of a phthalimide into the corresponding primary amine.
has_obo_namespace: RXNO
id: RXNO:0000419

Axiom
annotated source: phthalimide deprotection
annotated property: definition
annotated target: Conversion of a phthalimide into the corresponding primary amine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Kröhnke pyridine synthesis
type: Class
subclass of: pyridine synthesis
subclass of: Restriction
  on property: has specified product
  some values from: pyridines
definition: Condensation of a 1,5-diketone with ammonium acetate in acetic acid to form a pyridine.
database_cross_reference: http://dx.doi.org/10.1039/SP543
database_cross_reference: https://www.wikidata.org/wiki/Q2144364
has_exact_synonym: Krohnke pyridine synthesis
has_obo_namespace: RXNO
id: RXNO:0000420

Axiom
annotated source: Kröhnke pyridine synthesis
annotated property: definition
annotated target: Condensation of a 1,5-diketone with ammonium acetate in acetic acid to form a pyridine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Gattermann chlorination
type: Class
subclass of: Gattermann halogenation
subclass of: Restriction
  on property: has specified reactant
  some values from: hydrogen chloride
definition: A Gattermann halogenation where the aryl diazonium salt reacts with copper powder and hydrochloric acid to yield an aromatic chloride.
has_obo_namespace: RXNO
id: RXNO:0000421

Axiom
annotated source: Gattermann chlorination
annotated property: definition
annotated target: A Gattermann halogenation where the aryl diazonium salt reacts with copper powder and hydrochloric acid to yield an aromatic chloride.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Gattermann bromination
type: Class
subclass of: Gattermann halogenation
subclass of: Restriction
  on property: has specified reactant
  some values from: hydrogen bromide
definition: A Gattermann halogenation where the aryl diazonium salt reacts with copper powder and hydrobromic acid to yield an aromatic bromide.
has_obo_namespace: RXNO
id: RXNO:0000422

Axiom
annotated source: Gattermann bromination
annotated property: definition
annotated target: A Gattermann halogenation where the aryl diazonium salt reacts with copper powder and hydrobromic acid to yield an aromatic bromide.
database_cross_reference: https://orcid.org/0000-0002-4077-4719

aldehyde Barbier reaction
type: Class
subclass of: Barbier reaction
subclass of: Restriction
  on property: has specified product
  some values from: secondary alcohol
definition: A joining reaction between an aldehyde and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a secondary alcohol.
has_obo_namespace: RXNO
id: RXNO:0000426

Axiom
annotated source: aldehyde Barbier reaction
annotated property: definition
annotated target: A joining reaction between an aldehyde and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a secondary alcohol.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

ketone Barbier reaction
type: Class
subclass of: Barbier reaction
subclass of: Restriction
  on property: has specified product
  some values from: tertiary alcohol
definition: A joining reaction between an ketone and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a tertiary alcohol.
has_obo_namespace: RXNO
id: RXNO:0000427

Axiom
annotated source: ketone Barbier reaction
annotated property: definition
annotated target: A joining reaction between an ketone and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a tertiary alcohol.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

pivaloyl protection
type: Class
subclass of: hydroxyl group protection
subclass of: Restriction
  on property: has specified product
  some values from: pivalate ester
definition: Protection of a hydroxy group by reaction with pivaloyl chloride, resulting in formation of a pivaloyl ester.
has_obo_namespace: RXNO
id: RXNO:0000428

Axiom
annotated source: pivaloyl protection
annotated property: definition
annotated target: Protection of a hydroxy group by reaction with pivaloyl chloride, resulting in formation of a pivaloyl ester.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

pivaloyl deprotection
type: Class
subclass of: hydroxy group deprotection
subclass of: Restriction
  on property: deprotects
  some values from: hydroxy group
subclass of: Restriction
  on property: has specified reactant
  some values from: pivalate ester
definition: A hydroxy group deprotection where a pivalate group is removed in acid or base conditions.
has_obo_namespace: RXNO
id: RXNO:0000429

Axiom
annotated source: pivaloyl deprotection
annotated property: definition
annotated target: A hydroxy group deprotection where a pivalate group is removed in acid or base conditions.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

hydroxy group deprotection
type: Class
equivalent class: Class
  intersection of: deprotection reaction
  intersection of: Restriction
    on property: deprotects
    some values from: hydroxy group
subclass of: deprotection reaction
subclass of: Restriction
  on property: deprotects
  some values from: hydroxy group
definition: A deprotection reaction where the reactive centre is an oxygen atom.
has_exact_synonym: alcohol deprotection
has_obo_namespace: RXNO
id: RXNO:0000430

Axiom
annotated source: hydroxy group deprotection
annotated property: definition
annotated target: A deprotection reaction where the reactive centre is an oxygen atom.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

carboxylic acid to primary alcohol reduction
type: Class
subclass of: reduction
subclass of: Restriction
  on property: has participant beginning to exist
  some values from: primary alcohol
subclass of: Restriction
  on property: has participant ceasing to exist
  some values from: carboxylic acid
definition: A carboxylic acid reduction where the product is the corresponding primary alcohol.
has_obo_namespace: RXNO
id: RXNO:0000431

Axiom
annotated source: carboxylic acid to primary alcohol reduction
annotated property: definition
annotated target: A carboxylic acid reduction where the product is the corresponding primary alcohol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

tert-butyl protection
type: Class
subclass of: carboxylic acid protection
subclass of: Restriction
  on property: protects
  some values from: carboxy group
definition: A carboxy group protection where the product is a tert-butyl ester.
has_obo_namespace: RXNO
id: RXNO:0000432

Axiom
annotated source: tert-butyl protection
annotated property: definition
annotated target: A carboxy group protection where the product is a tert-butyl ester.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

carboxy group deprotection
type: Class
equivalent class: Class
  intersection of: deprotection reaction
  intersection of: Restriction
    on property: deprotects
    some values from: carboxy group
subclass of: deprotection reaction
subclass of: Restriction
  on property: deprotects
  some values from: carboxy group
definition: A deprotection reaction where the reactive centre is a carboxy oxygen atom.
has_obo_namespace: RXNO
id: RXNO:0000433

Axiom
annotated source: carboxy group deprotection
annotated property: definition
annotated target: A deprotection reaction where the reactive centre is a carboxy oxygen atom.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

tert-butyl ester deprotection
type: Class
subclass of: carboxy group deprotection
subclass of: Restriction
  on property: deprotects
  some values from: carboxy group
definition: A deprotection reaction where the reactant is a tert-butyl ester and the product is a carboxylic acid.
has_obo_namespace: RXNO
id: RXNO:0000434

Axiom
annotated source: tert-butyl ester deprotection
annotated property: definition
annotated target: A deprotection reaction where the reactant is a tert-butyl ester and the product is a carboxylic acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

methyl ester deprotection
type: Class
subclass of: carboxy group deprotection
subclass of: Restriction
  on property: deprotects
  some values from: carboxy group
definition: A deprotection reaction where the reactant is a methyl ester and the product is a carboxylic acid.
has_obo_namespace: RXNO
id: RXNO:0000435

Axiom
annotated source: methyl ester deprotection
annotated property: definition
annotated target: A deprotection reaction where the reactant is a methyl ester and the product is a carboxylic acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

ethyl ester deprotection
type: Class
subclass of: carboxy group deprotection
subclass of: Restriction
  on property: deprotects
  some values from: carboxy group
definition: A deprotection reaction where the reactant is an ethyl ester and the product is a carboxylic acid.
has_obo_namespace: RXNO
id: RXNO:0000436

Axiom
annotated source: ethyl ester deprotection
annotated property: definition
annotated target: A deprotection reaction where the reactant is an ethyl ester and the product is a carboxylic acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

molecular transformation objective
type: Class
subclass of: objective specification
definition: An objective specification that describes how a molecule's skeleton and substituents are to be transformed by a given experiment.
has_obo_namespace: RXNO
id: RXNO:0000437

Axiom
annotated source: molecular transformation objective
annotated property: definition
annotated target: An objective specification that describes how a molecule's skeleton and substituents are to be transformed by a given experiment.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

molecular skeleton cleaving objective
type: Class
subclass of: molecular transformation objective
definition: A molecular transformation specification that specifies that atoms should be lost from the molecular skeleton.
has_obo_namespace: RXNO
id: RXNO:0000438

Axiom
annotated source: molecular skeleton cleaving objective
annotated property: definition
annotated target: A molecular transformation specification that specifies that atoms should be lost from the molecular skeleton.
database_cross_reference: RSC:db

molecular ring formation objective
type: Class
subclass of: molecular transformation objective
definition: A molecular transformation specification that specifies that the product should contain a ring that was not in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000439

Axiom
annotated source: molecular ring formation objective
annotated property: definition
annotated target: A molecular transformation specification that specifies that the product should contain a ring that was not in any of the reactants.
database_cross_reference: RSC:db

molecular skeleton joining objective
type: Class
subclass of: molecular transformation objective
definition: A molecular transformation specification that specifies that atoms should be added to the molecular skeleton.
has_obo_namespace: RXNO
id: RXNO:0000440

Axiom
annotated source: molecular skeleton joining objective
annotated property: definition
annotated target: A molecular transformation specification that specifies that atoms should be added to the molecular skeleton.
database_cross_reference: RSC:db

molecular rearrangement objective
type: Class
subclass of: molecular transformation objective
definition: A molecular transformation specification that specifies that the number of rings and number of skeletal atoms should be preserved and that one or more atoms or groups of atoms move from one atom to another.
has_obo_namespace: RXNO
id: RXNO:0000441

Axiom
annotated source: molecular rearrangement objective
annotated property: definition
annotated target: A molecular transformation specification that specifies that the number of rings and number of skeletal atoms should be preserved and that one or more atoms or groups of atoms move from one atom to another.
database_cross_reference: RSC:db

functional modification objective
type: Class
subclass of: molecular transformation objective
definition: A molecular transformation specification that specifies that the substituents of a molecule should be changed but the number of atoms in the skeleton and their connectivity, but not necessarily the bond orders, should remain the same.
has_obo_namespace: RXNO
id: RXNO:0000442

Axiom
annotated source: functional modification objective
annotated property: definition
annotated target: A molecular transformation specification that specifies that the substituents of a molecule should be changed but the number of atoms in the skeleton and their connectivity, but not necessarily the bond orders, should remain the same.
database_cross_reference: RSC:db

Sakurai reaction
type: Class
equivalent class: Class
  union of: Sakurai reaction, aldehyde or ketone
  union of: Sakurai reaction, enone
  union of: Sakurai reaction, acid chloride
  union of: Sakurai reaction, acetal or ketal
  union of: imine Sakurai reaction
  union of: Sakurai reaction, epoxide
subclass of: allylation
subclass of: carbon-carbon coupling reaction
definition: Reaction of allyltrimethylsilane with a carbon electrophile to allylate the carbon electrophile.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r383/
database_cross_reference: https://www.wikidata.org/wiki/Q903031
has_exact_synonym: Hosomi-Sakurai reaction
has_obo_namespace: RXNO
id: RXNO:0000443

Axiom
annotated source: Sakurai reaction
annotated property: definition
annotated target: Reaction of allyltrimethylsilane with a carbon electrophile to allylate the carbon electrophile.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Fries rearrangement
type: Class
equivalent class: Class
  union of: ortho-Fries rearrangement
  union of: para-Fries rearrangement
subclass of: rearrangement step
subclass of: Restriction
  on property: has_part
  some values from: Lewis acid catalysis
definition: Rearrangement of the acyl group in a phenolate ester to the ortho- and/or para-position. It is catalysed by a Lewis acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r160/
database_cross_reference: https://www.wikidata.org/wiki/Q574893
has_exact_synonym: photo-Fries rearrangement
has_obo_namespace: RXNO
id: RXNO:0000444
comment: Can be promoted by heat or UV. The UV version (photo-Fries) involves a radical mechanism.

Axiom
annotated source: Fries rearrangement
annotated property: definition
annotated target: Rearrangement of the acyl group in a phenolate ester to the ortho- and/or para-position. It is catalysed by a Lewis acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

ortho-Fries rearrangement
type: Class
subclass of: Fries rearrangement
definition: Rearrangement of the acyl group in a phenolate ester to the ortho-position.
has_obo_namespace: RXNO
id: RXNO:0000445

Axiom
annotated source: ortho-Fries rearrangement
annotated property: definition
annotated target: Rearrangement of the acyl group in a phenolate ester to the ortho-position.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

para-Fries rearrangement
type: Class
subclass of: Fries rearrangement
definition: Rearrangement of the acyl group in a phenolate ester to the para-position.
has_obo_namespace: RXNO
id: RXNO:0000446

Axiom
annotated source: para-Fries rearrangement
annotated property: definition
annotated target: Rearrangement of the acyl group in a phenolate ester to the para-position.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Duff reaction
type: Class
subclass of: formylation
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: aromatic amine
definition: Formylation of a phenol or aromatic amine with hexamethylenetetramine in acidic conditions.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r119/
database_cross_reference: https://www.wikidata.org/wiki/Q903217
has_obo_namespace: RXNO
id: RXNO:0000447

Axiom
annotated source: Duff reaction
annotated property: definition
annotated target: Formylation of a phenol or aromatic amine with hexamethylenetetramine in acidic conditions.
database_cross_reference: https://doi.org/10.1039/JR9450000276
database_cross_reference: https://doi.org/10.1039/jr9410000547

molecular chain lengthening objective
type: Class
subclass of: molecular skeleton joining objective
definition: A molecular skeleton joining adjective that is satisfied by a chain part of a molecular skeleton being lengthened.
has_obo_namespace: RXNO
id: RXNO:0000448

Axiom
annotated source: molecular chain lengthening objective
annotated property: definition
annotated target: A molecular skeleton joining adjective that is satisfied by a chain part of a molecular skeleton being lengthened.
database_cross_reference: RSC:xp

molecular ring breaking objective
type: Class
subclass of: molecular transformation objective
definition: A molecular skeleton transformation objective that is satisfied by a reaction where the product has fewer rings than the reactants.
has_obo_namespace: RXNO
id: RXNO:0000449

Axiom
annotated source: molecular ring breaking objective
annotated property: definition
annotated target: A molecular skeleton transformation objective that is satisfied by a reaction where the product has fewer rings than the reactants.
database_cross_reference: RSC:xp

molecular ring contraction objective
type: Class
subclass of: molecular transformation objective
definition: A molecular skeleton transformation objective that is satisfied by a reaction where an existing ring is reduced in size.
has_obo_namespace: RXNO
id: RXNO:0000450

Axiom
annotated source: molecular ring contraction objective
annotated property: definition
annotated target: A molecular skeleton transformation objective that is satisfied by a reaction where an existing ring is reduced in size.
database_cross_reference: RSC:xp

aldehyde Sakurai reaction
type: Class
subclass of: Sakurai reaction, aldehyde or ketone
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: A carbon-carbon coupling reaction in which an aldehyde reacts with allyltrimethylsilane to form a homoallylic alcohol.
has_obo_namespace: RXNO
id: RXNO:0000451

Axiom
annotated source: aldehyde Sakurai reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction in which an aldehyde reacts with allyltrimethylsilane to form a homoallylic alcohol.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

ketone Sakurai reaction
type: Class
subclass of: Sakurai reaction, aldehyde or ketone
subclass of: Restriction
  on property: has specified reactant
  some values from: ketone
definition: A carbon-carbon coupling reaction in which a ketone reacts with allyltrimethylsilane to form a homoallylic alcohol.
has_obo_namespace: RXNO
id: RXNO:0000452

Axiom
annotated source: ketone Sakurai reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction in which a ketone reacts with allyltrimethylsilane to form a homoallylic alcohol.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

functional group modification objective
type: Class
subclass of: functional modification objective
definition: A molecular skeleton transformation objective that is satisfied by a reaction in which a functional group undergoes a change that does not affect the number of atoms in (or connectivity of) the skeleton of the molecule.
has_obo_namespace: RXNO
id: RXNO:0000453

Axiom
annotated source: functional group modification objective
annotated property: definition
annotated target: A molecular skeleton transformation objective that is satisfied by a reaction in which a functional group undergoes a change that does not affect the number of atoms in (or connectivity of) the skeleton of the molecule.
database_cross_reference: RSC:xp

end-of-chain chain shortening objective
type: Class
subclass of: molecular skeleton cleaving objective
definition: A molecular skeleton transformation objective that is satisfied by a reaction in which a single skeletal atom is removed from the end of a chain.
has_obo_namespace: RXNO
id: RXNO:0000454

Axiom
annotated source: end-of-chain chain shortening objective
annotated property: definition
annotated target: A molecular skeleton transformation objective that is satisfied by a reaction in which a single skeletal atom is removed from the end of a chain.
database_cross_reference: RSC:xp

functional reduction objective
type: Class
subclass of: functional group modification objective
definition: A functional group modification objective that is satisfied by a reaction in which a functional group is reduced.
has_obo_namespace: RXNO
id: RXNO:0000455

Axiom
annotated source: functional reduction objective
annotated property: definition
annotated target: A functional group modification objective that is satisfied by a reaction in which a functional group is reduced.
database_cross_reference: RSC:xp

addition objective
type: Class
subclass of: functional modification objective
definition: A functional modification objective that is satisfied by a reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order.
has_obo_namespace: RXNO
id: RXNO:0000456

Axiom
annotated source: addition objective
annotated property: definition
annotated target: A functional modification objective that is satisfied by a reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order.
database_cross_reference: RSC:xp

molecular ring expansion objective
type: Class
subclass of: molecular transformation objective
definition: A molecular transformation objective that is satisfied by a reaction in which an existing skeletal ring is increased in size.
has_obo_namespace: RXNO
id: RXNO:0000457

Axiom
annotated source: molecular ring expansion objective
annotated property: definition
annotated target: A molecular transformation objective that is satisfied by a reaction in which an existing skeletal ring is increased in size.
database_cross_reference: RSC:xp

molecular ring rearrangement objective
type: Class
subclass of: molecular transformation objective
definition: A molecular transformation objective that is satisfied by a reaction in which the number of skeletal rings in a molecule stays the same but the connectivity of the atoms in at least one ring changes.
has_obo_namespace: RXNO
id: RXNO:0000458

Axiom
annotated source: molecular ring rearrangement objective
annotated property: definition
annotated target: A molecular transformation objective that is satisfied by a reaction in which the number of skeletal rings in a molecule stays the same but the connectivity of the atoms in at least one ring changes.
database_cross_reference: RSC:xp

acetoacetic ester synthesis
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular skeleton joining objective
subclass of: Restriction
  on property: has specified product
  some values from: carboxylic ester
subclass of: Restriction
  on property: has specified reactant
  some values from: haloalkane
subclass of: Restriction
  on property: has specified reactant
  some values from: beta-ketoester
definition: A carbon-carbon coupling reaction between a beta-ketoester and an alkyl halide to yield an alpha-alkylated ester.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r1/
database_cross_reference: https://www.wikidata.org/wiki/Q1017086
has_obo_namespace: RXNO
id: RXNO:0000459
comment: Subsequent treatment with mild hydrolysis leads to a ketone; concentrated base produces a substituted ester.

Axiom
annotated source: acetoacetic ester synthesis
annotated property: definition
annotated target: A carbon-carbon coupling reaction between a beta-ketoester and an alkyl halide to yield an alpha-alkylated ester.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

intramolecular acyloin condensation
type: Class
subclass of: ring formation reaction step
subclass of: acyloin condensation
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular ring formation objective
definition: A reductive coupling reaction between two ester groups in the same molecule to give an acyloin (an alpha-hydroxyketone).
has_obo_namespace: RXNO
id: RXNO:0000460

Axiom
annotated source: intramolecular acyloin condensation
annotated property: definition
annotated target: A reductive coupling reaction between two ester groups in the same molecule to give an acyloin (an alpha-hydroxyketone).
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

intermolecular acyloin condensation
type: Class
subclass of: acyloin condensation
subclass of: Restriction
  on property: achieves_planned_objective
  some values from: molecular skeleton joining objective
definition: A reductive coupling reaction between two ester groups in different molecules to give an acyloin (an alpha-hydroxyketone).
has_obo_namespace: RXNO
id: RXNO:0000461

Axiom
annotated source: intermolecular acyloin condensation
annotated property: definition
annotated target: A reductive coupling reaction between two ester groups in different molecules to give an acyloin (an alpha-hydroxyketone).
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0002-4077-4719

molecular extrusion objective
type: Class
subclass of: molecular skeleton cleaving objective
definition: A molecular transformation objective that is satisfied by a cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule.
has_obo_namespace: RXNO
id: RXNO:0000462

Axiom
annotated source: molecular extrusion objective
annotated property: definition
annotated target: A molecular transformation objective that is satisfied by a cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule.
database_cross_reference: RSC:xp

molecular fragmentation objective
type: Class
subclass of: molecular skeleton cleaving objective
definition: A molecular transformation objective that is satisfied by a reaction in which the parent molecule breaks up into three or more products.
has_obo_namespace: RXNO
id: RXNO:0000463

Axiom
annotated source: molecular fragmentation objective
annotated property: definition
annotated target: A molecular transformation objective that is satisfied by a reaction in which the parent molecule breaks up into three or more products.
database_cross_reference: RSC:xp

Pauson-Khand reaction
type: Class
subclass of: [2+2+1] cycloaddition
definition: A [2+2+1] cycloaddition between an alkyne, an alkene and carbon monoxide to form an alpha-beta-unsaturated cyclopentenone.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r320/
database_cross_reference: https://www.wikidata.org/wiki/Q903694
has_obo_namespace: RXNO
id: RXNO:0000464

Axiom
annotated source: Pauson-Khand reaction
annotated property: definition
annotated target: A [2+2+1] cycloaddition between an alkyne, an alkene and carbon monoxide to form an alpha-beta-unsaturated cyclopentenone.
database_cross_reference: doi:10.1039/P19730000975

fused-ring-system formation objective
type: Class
subclass of: molecular ring formation objective
definition: A molecular transformation objective that is satisfied by a reaction in which a fused ring system is present in a product that was not present in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000465

Axiom
annotated source: fused-ring-system formation objective
annotated property: definition
annotated target: A molecular transformation objective that is satisfied by a reaction in which a fused ring system is present in a product that was not present in any of the reactants.
database_cross_reference: RSC:xp

polymerisation objective
type: Class
subclass of: molecular skeleton joining objective
definition: A molecular transformation objective that is satisfied by a reaction in which a large number of monomers react together to product a polymer consisting of repeating units.
has_obo_namespace: RXNO
id: RXNO:0000466

Axiom
annotated source: polymerisation objective
annotated property: definition
annotated target: A molecular transformation objective that is satisfied by a reaction in which a large number of monomers react together to product a polymer consisting of repeating units.
database_cross_reference: RSC:xp

Algar-Flynn-Oyamada reaction
type: Class
subclass of: fused-ring-system formation
subclass of: oxacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: flavonols
subclass of: Restriction
  on property: has specified reactant
  some values from: hydrogen peroxide
subclass of: Restriction
  on property: has specified reactant
  some values from: chalcones
definition: A fused-ring-system formation reaction where a flavonol is produced by oxidation of a chalcone with alkaline hydrogen peroxide.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r5/
database_cross_reference: https://www.wikidata.org/wiki/Q903717
has_obo_namespace: RXNO
id: RXNO:0000467
comment: definition source Merck Index

Axiom
annotated source: Algar-Flynn-Oyamada reaction
annotated property: definition
annotated target: A fused-ring-system formation reaction where a flavonol is produced by oxidation of a chalcone with alkaline hydrogen peroxide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

molecular substitution objective
type: Class
subclass of: functional modification objective
definition: A molecular transformation objective that is satisfied by a reaction in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent.
has_obo_namespace: RXNO
id: RXNO:0000468

Axiom
annotated source: molecular substitution objective
annotated property: definition
annotated target: A molecular transformation objective that is satisfied by a reaction in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent.
database_cross_reference: RSC:xp

Allan-Robinson flavone synthesis
type: Class
subclass of: Allan-Robinson reaction
subclass of: Restriction
  on property: has specified product
  some values from: flavones
subclass of: Restriction
  on property: has specified reactant
  some values from: carboxylic anhydride
definition: Reaction of ortho-hydroxyaryl ketones with aromatic carboxylic acid anhydrides to yield a flavone.
has_obo_namespace: RXNO
id: RXNO:0000470

Axiom
annotated source: Allan-Robinson flavone synthesis
annotated property: definition
annotated target: Reaction of ortho-hydroxyaryl ketones with aromatic carboxylic acid anhydrides to yield a flavone.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Allan-Robinson isoflavone synthesis
type: Class
subclass of: Allan-Robinson reaction
subclass of: Restriction
  on property: has specified product
  some values from: isoflavones
subclass of: Restriction
  on property: has specified reactant
  some values from: carboxylic anhydride
definition: Reaction of ortho-hydroxyaryl ketones with aromatic carboxylic acid anhydrides to yield an isoflavone.
has_obo_namespace: RXNO
id: RXNO:0000471

Axiom
annotated source: Allan-Robinson isoflavone synthesis
annotated property: definition
annotated target: Reaction of ortho-hydroxyaryl ketones with aromatic carboxylic acid anhydrides to yield an isoflavone.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Amadori rearrangement
type: Class
subclass of: rearrangement step
definition: Rearrangement of an aldose N-glycoside to a ketose N-glycoside by acid or base catalysis.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r8/
database_cross_reference: https://www.wikidata.org/wiki/Q452196
has_obo_namespace: RXNO
id: RXNO:0000472
comment: definition source Merck Index

Axiom
annotated source: Amadori rearrangement
annotated property: definition
annotated target: Rearrangement of an aldose N-glycoside to a ketose N-glycoside by acid or base catalysis.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Arens-van Dorp synthesis
type: Class
subclass of: molecular skeleton joining reaction
definition: Reaction of a ketone with ethoxyacetylene to form an alkoxyethynyl alcohol.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r9/
database_cross_reference: https://www.wikidata.org/wiki/Q16624458
has_obo_namespace: RXNO
id: RXNO:0000473

Axiom
annotated source: Arens-van Dorp synthesis
annotated property: definition
annotated target: Reaction of a ketone with ethoxyacetylene to form an alkoxyethynyl alcohol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r9/

Auwers synthesis
type: Class
subclass of: ring expansion
subclass of: oxacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: flavonols
definition: Ring expansion of a 2-bromo-2-(alpha-bromobenzyl)-1-benzofuran to a flavonol in alcoholic alkali.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r11/
database_cross_reference: https://www.wikidata.org/wiki/Q3115850
has_obo_namespace: RXNO
id: RXNO:0000474

Axiom
annotated source: Auwers synthesis
annotated property: definition
annotated target: Ring expansion of a 2-bromo-2-(alpha-bromobenzyl)-1-benzofuran to a flavonol in alcoholic alkali.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r11/

Allan-Robinson reaction
type: Class
equivalent class: Class
  union of: Allan-Robinson flavone synthesis
  union of: Allan-Robinson isoflavone synthesis
subclass of: fused-ring-system formation
subclass of: oxacycle synthesis
definition: Reaction of ortho-hydroxyaryl ketones with aromatic acid anhydrides to yield a flavone or isoflavone.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r6/
database_cross_reference: https://www.wikidata.org/wiki/Q3046015
has_obo_namespace: RXNO
id: RXNO:0000475

Axiom
annotated source: Allan-Robinson reaction
annotated property: definition
annotated target: Reaction of ortho-hydroxyaryl ketones with aromatic acid anhydrides to yield a flavone or isoflavone.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r6/

Meyer-Schuster rearrangement
type: Class
subclass of: rearrangement step
subclass of: Restriction
  on property: has_intermediate
  some values from: allenes
definition: Rearrangement of a propargyl alcohol to an alpha,beta-unsaturated carbonyl compound via an allene intermediate to yield the gamma-substituted product.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r278/
database_cross_reference: https://www.wikidata.org/wiki/Q902668
has_obo_namespace: RXNO
id: RXNO:0000476

Axiom
annotated source: Meyer-Schuster rearrangement
annotated property: definition
annotated target: Rearrangement of a propargyl alcohol to an alpha,beta-unsaturated carbonyl compound via an allene intermediate to yield the gamma-substituted product.
database_cross_reference: https://doi.org/10.1039/b912099h

Rupe rearrangement
type: Class
subclass of: rearrangement step
subclass of: Restriction
  on property: has_intermediate
  some values from: enyne
definition: Rearrangement of a propargyl alcohol to an alpha,beta-unsaturated carbonyl compound via an enyne intermediate to yield the beta-substituted product.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r278/
has_obo_namespace: RXNO
id: RXNO:0000477

Axiom
annotated source: Rupe rearrangement
annotated property: definition
annotated target: Rearrangement of a propargyl alcohol to an alpha,beta-unsaturated carbonyl compound via an enyne intermediate to yield the beta-substituted product.
database_cross_reference: https://doi.org/10.1039/b912099h

Still-Gennari modification
type: Class
subclass of: Horner-Wadsworth-Emmons reaction
definition: A Horner-Wadsworth-Emmons reaction that uses phosphonates with electron-withdrawing groups and dissociating conditions to produce predominantly Z-olefins.
has_exact_synonym: Still modification
has_obo_namespace: RXNO
id: RXNO:0000478

Axiom
annotated source: Still-Gennari modification
annotated property: definition
annotated target: A Horner-Wadsworth-Emmons reaction that uses phosphonates with electron-withdrawing groups and dissociating conditions to produce predominantly Z-olefins.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

olefination
type: Class
equivalent class: Class
  intersection of: carbon-carbon coupling reaction
  intersection of: Restriction
    on property: has specified product
    some values from: olefin
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified product
  some values from: olefin
definition: A molecular skeleton joining reaction where the connection formed is a carbon-carbon double bond.
has_obo_namespace: RXNO
id: RXNO:0000479

Axiom
annotated source: olefination
annotated property: definition
annotated target: A molecular skeleton joining reaction where the connection formed is a carbon-carbon double bond.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Tebbe olefination
type: Class
subclass of: olefination
definition: Reaction of an aldehyde or ketone or carboxylic ester or amide with the Tebbe reagent to yield an olefin or an enol ether or an enamine.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r428/
has_obo_namespace: RXNO
id: RXNO:0000480

Axiom
annotated source: Tebbe olefination
annotated property: definition
annotated target: Reaction of an aldehyde or ketone or carboxylic ester or amide with the Tebbe reagent to yield an olefin or an enol ether or an enamine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r428/

Myers-Saito cyclisation
type: Class
subclass of: ring formation reaction step
definition: Cyclization of a enynyl allene to yield a toluene biradical with radical centres on the methyl group and at the meta position.
created by: batchelorc
creation date: 2014-02-28T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r292/
database_cross_reference: https://www.wikidata.org/wiki/Q89925623
has_exact_synonym: Myers-Saito cyclization
has_exact_synonym: Myers-Saito process
has_exact_synonym: Myers-Saito reaction
has_obo_namespace: RXNO
id: RXNO:0000481

Axiom
annotated source: Myers-Saito cyclisation
annotated property: definition
annotated target: Cyclization of a enynyl allene to yield a toluene biradical with radical centres on the methyl group and at the meta position.
database_cross_reference: https://doi.org/10.1039/b009965l
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Schmittel cyclisation
type: Class
subclass of: ring formation reaction step
definition: Cyclization of a enynyl allene to yield a 1-methyl-5-methylenecyclopenta-1,3-diene biradical with radical centres on the methyl group and methylene group.
created by: batchelorc
creation date: 2014-02-28T09:00:00Z
has_exact_synonym: Schmittel cyclization
has_obo_namespace: RXNO
id: RXNO:0000482

Axiom
annotated source: Schmittel cyclisation
annotated property: definition
annotated target: Cyclization of a enynyl allene to yield a 1-methyl-5-methylenecyclopenta-1,3-diene biradical with radical centres on the methyl group and methylene group.
database_cross_reference: https://doi.org/10.1039/b009965l
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Baudisch reaction
type: Class
subclass of: functional group addition step
definition: Copper-catalysed reaction of benzene with a nitrosylating agent and hydrogen peroxide to form an o-nitrosophenol.
created by: batchelorc
creation date: 2014-02-28T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r26/
database_cross_reference: https://www.wikidata.org/wiki/Q3536586
has_obo_namespace: RXNO
id: RXNO:0000483

Axiom
annotated source: Baudisch reaction
annotated property: definition
annotated target: Copper-catalysed reaction of benzene with a nitrosylating agent and hydrogen peroxide to form an o-nitrosophenol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

deprotection objective
type: Class
subclass of: functional modification objective
definition: A functional modification objective that is satisfied by deprotecting some functional group.
created by: batchelorc
creation date: 2014-02-28T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000484

Axiom
annotated source: deprotection objective
annotated property: definition
annotated target: A functional modification objective that is satisfied by deprotecting some functional group.
database_cross_reference: RSC:xp

protection objective
type: Class
subclass of: functional modification objective
definition: A functional modification objective that is satisfied by protecting some functional group.
created by: batchelorc
creation date: 2014-02-28T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000485

Axiom
annotated source: protection objective
annotated property: definition
annotated target: A functional modification objective that is satisfied by protecting some functional group.
database_cross_reference: RSC:xp

molecular skeleton elimination objective
type: Class
subclass of: functional modification objective
definition: A functional modification objective that is satisfied by a reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order.
created by: batchelorc
creation date: 2014-02-28T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000486

Axiom
annotated source: molecular skeleton elimination objective
annotated property: definition
annotated target: A functional modification objective that is satisfied by a reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order.
database_cross_reference: RSC:xp

molecular skeleton insertion objective
type: Class
subclass of: molecular skeleton joining objective
definition: A molecular skeleton joining objective that is satisfied by a reaction in which one or more atoms are added to the middle of a chain.
created by: batchelorc
creation date: 2014-02-28T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000487

Axiom
annotated source: molecular skeleton insertion objective
annotated property: definition
annotated target: A molecular skeleton joining objective that is satisfied by a reaction in which one or more atoms are added to the middle of a chain.
database_cross_reference: RSC:xp

joining with rearrangement objective
type: Class
subclass of: molecular skeleton joining objective
definition: A molecular skeleton joining objective that is satisfied by a reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs.
created by: batchelorc
creation date: 2014-02-28T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000488

Axiom
annotated source: joining with rearrangement objective
annotated property: definition
annotated target: A molecular skeleton joining objective that is satisfied by a reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs.
database_cross_reference: RSC:xp

functional group addition objective
type: Class
subclass of: functional modification objective
definition: A functional modification objective that is satisfied by a reaction in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged.
created by: batchelorc
creation date: 2014-02-28T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000489

Axiom
annotated source: functional group addition objective
annotated property: definition
annotated target: A functional modification objective that is satisfied by a reaction in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged.
database_cross_reference: RSC:xp

functional oxidation objective
type: Class
subclass of: functional group modification objective
definition: A functional group modification objective that is satisfied by a reaction in which a functional group is oxidised.
created by: batchelorc
creation date: 2014-02-28T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000490

Axiom
annotated source: functional oxidation objective
annotated property: definition
annotated target: A functional group modification objective that is satisfied by a reaction in which a functional group is oxidised.
database_cross_reference: RSC:xp

interrupted Nazarov cyclisation
type: Class
subclass of: ring formation reaction step
subclass of: Restriction
  on property: has_part
  some values from: Nazarov cyclisation
definition: Cyclisation of a propargyl alpha,beta-unsaturated ketone where the reactant rearranges to an allenyl vinyl ketone, followed by a Nazarov cyclisation in which a nucleophile 'intercepts' the intermediate carbocation to yield a cyclopentenone substituted at the alpha position opposite the double bond.
created by: batchelorc
creation date: 2014-02-28T12:00:00Z
has_exact_synonym: interrupted Nazarov cyclization
has_obo_namespace: RXNO
id: RXNO:0000491

Axiom
annotated source: interrupted Nazarov cyclisation
annotated property: definition
annotated target: Cyclisation of a propargyl alpha,beta-unsaturated ketone where the reactant rearranges to an allenyl vinyl ketone, followed by a Nazarov cyclisation in which a nucleophile 'intercepts' the intermediate carbocation to yield a cyclopentenone substituted at the alpha position opposite the double bond.
database_cross_reference: doi:10.1039/c3cs60333d

Bamberger rearrangement
type: Class
subclass of: rearrangement step
definition: Rearrangement of an N-phenylhydroxamine in acid to yield a para-aminophenol.
created by: batchelorc
creation date: 2014-03-03T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r15/
database_cross_reference: https://www.wikidata.org/wiki/Q139251
has_obo_namespace: RXNO
id: RXNO:0000492

Axiom
annotated source: Bamberger rearrangement
annotated property: definition
annotated target: Rearrangement of an N-phenylhydroxamine in acid to yield a para-aminophenol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r15/

Bart reaction
type: Class
subclass of: aromatic substitution step
definition: Reaction of an aromatic diazonium compound with an alkali arsenite in the presence of copper or silver to yield an aromatic arsonic acid.
created by: batchelorc
creation date: 2014-03-03T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r19/
has_obo_namespace: RXNO
id: RXNO:0000493

Axiom
annotated source: Bart reaction
annotated property: definition
annotated target: Reaction of an aromatic diazonium compound with an alkali arsenite in the presence of copper or silver to yield an aromatic arsonic acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r19/

Bartoli indole synthesis
type: Class
subclass of: indole synthesis
subclass of: Restriction
  on property: has specified product
  some values from: indoles
definition: Reaction of an ortho-substituted nitroarene with a vinyl Grignard reagent to yield a 7-substituted indole.
created by: batchelorc
creation date: 2014-03-03T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r20/
database_cross_reference: https://www.wikidata.org/wiki/Q3508929
has_obo_namespace: RXNO
id: RXNO:0000494

Axiom
annotated source: Bartoli indole synthesis
annotated property: definition
annotated target: Reaction of an ortho-substituted nitroarene with a vinyl Grignard reagent to yield a 7-substituted indole.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Barton olefination
type: Class
subclass of: olefination
definition: Reaction of an aldehyde or ketone with a thioaldehyde or thioketone via a 1,3,4-thiadiazoline intermediate to yield an olefin.
created by: batchelorc
creation date: 2014-03-03T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r23/
has_exact_synonym: Barton olefin synthesis
has_obo_namespace: RXNO
id: RXNO:0000495

Axiom
annotated source: Barton olefination
annotated property: definition
annotated target: Reaction of an aldehyde or ketone with a thioaldehyde or thioketone via a 1,3,4-thiadiazoline intermediate to yield an olefin.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Barton-Zard reaction
type: Class
subclass of: pyrrole synthesis
subclass of: Restriction
  on property: has specified product
  some values from: pyrroles
definition: Reaction of a nitroalkene with an alpha-isocyanoacetate to yield a substituted pyrrole.
created by: batchelorc
creation date: 2014-03-03T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r25/
database_cross_reference: https://www.wikidata.org/wiki/Q4865733
has_exact_synonym: Barton-Zard synthesis
has_obo_namespace: RXNO
id: RXNO:0000496

Axiom
annotated source: Barton-Zard reaction
annotated property: definition
annotated target: Reaction of a nitroalkene with an alpha-isocyanoacetate to yield a substituted pyrrole.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

pyrrole synthesis
type: Class
equivalent class: Class
  intersection of: molecular process
  intersection of: Restriction
    on property: has specified product
    some values from: pyrroles
subclass of: azacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: pyrroles
definition: A reaction in which the intended product is a pyrrole that was not present in any of the reactants.
created by: batchelorc
creation date: 2014-03-03T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000497

Axiom
annotated source: pyrrole synthesis
annotated property: definition
annotated target: A reaction in which the intended product is a pyrrole that was not present in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Béchamp reduction
type: Class
subclass of: functional group reduction
subclass of: Restriction
  on property: has specified product
  some values from: aromatic amine
definition: Reduction of an aromatic nitro compound to the corresponding arene by iron in some form in aqueous acid.
created by: batchelorc
creation date: 2014-03-03T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r28/
database_cross_reference: https://www.wikidata.org/wiki/Q906075
has_exact_synonym: Bechamp reduction
has_obo_namespace: RXNO
id: RXNO:0000498

Axiom
annotated source: Béchamp reduction
annotated property: definition
annotated target: Reduction of an aromatic nitro compound to the corresponding arene by iron in some form in aqueous acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Beirut reaction
type: Class
subclass of: ring expansion
definition: Reaction of a benzofurazan 1-oxide with an enamine or enolate to yield a quinoxaline-1,4-dioxide.
created by: batchelorc
creation date: 2014-03-03T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r30/
has_obo_namespace: RXNO
id: RXNO:0000499
comment: definition source Merck Index

Axiom
annotated source: Beirut reaction
annotated property: definition
annotated target: Reaction of a benzofurazan 1-oxide with an enamine or enolate to yield a quinoxaline-1,4-dioxide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Bénary reaction
type: Class
subclass of: molecular skeleton joining reaction
definition: Reaction of a beta-aminovinylketone with a Grignard reagent to yield a substituted alpha,beta-unsaturated carbonyl compound.
created by: batchelorc
creation date: 2014-03-03T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r31/
database_cross_reference: https://www.wikidata.org/wiki/Q816687
has_exact_synonym: Benary reaction
has_obo_namespace: RXNO
id: RXNO:0000500

Axiom
annotated source: Bénary reaction
annotated property: definition
annotated target: Reaction of a beta-aminovinylketone with a Grignard reagent to yield a substituted alpha,beta-unsaturated carbonyl compound.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Feist-Bénary synthesis
type: Class
subclass of: oxacycle synthesis
subclass of: Restriction
  on property: has_participant
  some values from: pyridine
subclass of: Restriction
  on property: has specified product
  some values from: furans
definition: Reaction of an alpha-haloketone or alpha-haloether with a 1,3-dicarbonyl compound in the presence of pyridine to yield a substituted furan.
created by: batchelorc
creation date: 2014-03-03T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r138/
database_cross_reference: https://www.wikidata.org/wiki/Q5441589
has_obo_namespace: RXNO
id: RXNO:0000501

Axiom
annotated source: Feist-Bénary synthesis
annotated property: definition
annotated target: Reaction of an alpha-haloketone or alpha-haloether with a 1,3-dicarbonyl compound in the presence of pyridine to yield a substituted furan.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Boulton-Katritzky rearrangement
type: Class
equivalent class: Class
  union of: monocyclic Boulton-Katritzky rearrangement
  union of: bicyclic Boulton-Katritzky rearrangement
subclass of: ring rearrangement
definition: Rearrangement of a mancude eight-membered system containing a pentacycle into a different pentacycle where two of the ring atoms are ring atoms in the original molecule.
created by: batchelorc
creation date: 2014-03-04T09:00:00Z
database_cross_reference: https://www.wikidata.org/wiki/Q56298381
has_obo_namespace: RXNO
id: RXNO:0000502

Axiom
annotated source: Boulton-Katritzky rearrangement
annotated property: definition
annotated target: Rearrangement of a mancude eight-membered system containing a pentacycle into a different pentacycle where two of the ring atoms are ring atoms in the original molecule.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

monocyclic Boulton-Katritzky rearrangement
type: Class
subclass of: Boulton-Katritzky rearrangement
definition: Rearrangement of an azapentacycle containing a -N= system where there is an unsaturated three-heavy-atom substituent XYZ on the substituent double-bonded to the nitrogen, to a new azapentacycle where the pivotal nitrogen has broken its single bond and formed a new bond with atom Z.
created by: batchelorc
creation date: 2014-03-04T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000503

Axiom
annotated source: monocyclic Boulton-Katritzky rearrangement
annotated property: definition
annotated target: Rearrangement of an azapentacycle containing a -N= system where there is an unsaturated three-heavy-atom substituent XYZ on the substituent double-bonded to the nitrogen, to a new azapentacycle where the pivotal nitrogen has broken its single bond and formed a new bond with atom Z.
database_cross_reference: https://doi.org/10.1039/j39670002005

bicyclic Boulton-Katritzky rearrangement
type: Class
subclass of: Boulton-Katritzky rearrangement
definition: Rearrangement of a mancude bicyclo[4.3.0] compound with an unsaturated two-heavy-atom substituent on the six-membered ring alpha to the bridgehead to form a new mancude bicyclo[4.3.0] compound where the five-membered ring has been formed from the two-heavy-atom substituent and the original five-membered ring has been broken.
created by: batchelorc
creation date: 2014-03-04T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000504

Axiom
annotated source: bicyclic Boulton-Katritzky rearrangement
annotated property: definition
annotated target: Rearrangement of a mancude bicyclo[4.3.0] compound with an unsaturated two-heavy-atom substituent on the six-membered ring alpha to the bridgehead to form a new mancude bicyclo[4.3.0] compound where the five-membered ring has been formed from the two-heavy-atom substituent and the original five-membered ring has been broken.
database_cross_reference: https://doi.org/10.1039/j29660001004

Mukaiyama-Hoshino method
type: Class
subclass of: functional group modification
definition: Reaction of a primary nitro compound with phenyl isocynatate and triethylamine to yield a nitrile oxide.
created by: batchelorc
creation date: 2014-03-04T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000505

Axiom
annotated source: Mukaiyama-Hoshino method
annotated property: definition
annotated target: Reaction of a primary nitro compound with phenyl isocynatate and triethylamine to yield a nitrile oxide.
database_cross_reference: https://doi.org/10.1021/ja01505a017
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Nef synthesis
type: Class
subclass of: molecular skeleton joining reaction
definition: Reaction of an aldehyde or ketone with a sodium acetylide to yield a propargyl alcohol.
created by: batchelorc
creation date: 2014-03-04T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r298/
database_cross_reference: https://www.wikidata.org/wiki/Q16930708
has_obo_namespace: RXNO
id: RXNO:0000506

Axiom
annotated source: Nef synthesis
annotated property: definition
annotated target: Reaction of an aldehyde or ketone with a sodium acetylide to yield a propargyl alcohol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Krapcho decarboxylation
type: Class
subclass of: decarboxylation
subclass of: end-of-chain chain shortening
definition: Reaction of an ester with an electron-withdrawing group alpha- to the ester functionality with a metal halide or pseudohalide to yield the shorter homologous system.
created by: batchelorc
creation date: 2014-03-04T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r242/
database_cross_reference: https://www.wikidata.org/wiki/Q4597398
has_exact_synonym: Krapcho decarbalkoxylation
has_obo_namespace: RXNO
id: RXNO:0000507

Axiom
annotated source: Krapcho decarboxylation
annotated property: definition
annotated target: Reaction of an ester with an electron-withdrawing group alpha- to the ester functionality with a metal halide or pseudohalide to yield the shorter homologous system.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Cadogan cyclization
type: Class
subclass of: fused-ring-system formation
definition: Reaction of an aromatic nitro compound with an unsaturated substituent at the alpha-position to form a fused-ring nitrogen heterocycle.
created by: batchelorc
creation date: 2014-03-04T09:00:00Z
has_exact_synonym: Cadogan reaction
has_exact_synonym: Cadogan ring closure
has_exact_synonym: Cadogan ring-closure
has_obo_namespace: RXNO
id: RXNO:0000508

Axiom
annotated source: Cadogan cyclization
annotated property: definition
annotated target: Reaction of an aromatic nitro compound with an unsaturated substituent at the alpha-position to form a fused-ring nitrogen heterocycle.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Cadogan indole synthesis
type: Class
equivalent class: Class
  intersection of: Cadogan cyclization
  intersection of: Restriction
    on property: has specified product
    some values from: indoles
subclass of: indole synthesis
subclass of: Cadogan cyclization
subclass of: Restriction
  on property: has specified product
  some values from: indoles
definition: A Cadogan cyclization that results in an indole.
created by: batchelorc
creation date: 2014-03-05T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000509

Axiom
annotated source: Cadogan indole synthesis
annotated property: definition
annotated target: A Cadogan cyclization that results in an indole.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Benkeser reduction
type: Class
subclass of: hydrogenation
subclass of: addition reaction step
definition: Addition of hydrogen atoms to unsaturated rings by means of alkali metals in low-molecular weight amines.
created by: batchelorc
creation date: 2014-03-06T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r32/
has_exact_synonym: Benkeser reaction
has_obo_namespace: RXNO
id: RXNO:0000510

Axiom
annotated source: Benkeser reduction
annotated property: definition
annotated target: Addition of hydrogen atoms to unsaturated rings by means of alkali metals in low-molecular weight amines.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Madelung indole synthesis
type: Class
subclass of: molecular dehydration reaction
subclass of: indole synthesis
subclass of: Restriction
  on property: has specified product
  some values from: indoles
definition: Reaction of an N-(2-alkylphenyl)alkanamide with strong base to form an indole.
created by: batchelorc
creation date: 2014-03-07T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r261/
database_cross_reference: https://www.wikidata.org/wiki/Q2632831
has_exact_synonym: Madelung synthesis
has_obo_namespace: RXNO
id: RXNO:0000511

Axiom
annotated source: Madelung indole synthesis
annotated property: definition
annotated target: Reaction of an N-(2-alkylphenyl)alkanamide with strong base to form an indole.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Smith indole synthesis
type: Class
subclass of: indole synthesis
subclass of: Restriction
  on property: has specified product
  some values from: indoles
subclass of: Restriction
  on property: has specified reactant
  some values from: organolithium compound
definition: Reaction of a N-(2-alkylphenyl)-trimethylsilylamine with two equivalents of organolithium and an ester or carboxylic acid to form an indole.
created by: batchelorc
creation date: 2014-03-07T09:00:00Z
has_exact_synonym: Smith-modified Madelung synthesis
has_obo_namespace: RXNO
id: RXNO:0000512

Axiom
annotated source: Smith indole synthesis
annotated property: definition
annotated target: Reaction of a N-(2-alkylphenyl)-trimethylsilylamine with two equivalents of organolithium and an ester or carboxylic acid to form an indole.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Mumm rearrangement
type: Class
subclass of: rearrangement step
subclass of: Restriction
  on property: has specified product
  some values from: carboximides
definition: Rearrangement of an acyl imidate to form a carboximide.
created by: batchelorc
creation date: 2014-03-07T09:00:00Z
database_cross_reference: https://www.wikidata.org/wiki/Q723311
has_obo_namespace: RXNO
id: RXNO:0000513

Axiom
annotated source: Mumm rearrangement
annotated property: definition
annotated target: Rearrangement of an acyl imidate to form a carboximide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Chapman rearrangement
type: Class
subclass of: rearrangement step
definition: Rearrangement of an aryl imino ether to yield an N,N-diaryl amide.
created by: batchelorc
creation date: 2014-03-07T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r74/
has_obo_namespace: RXNO
id: RXNO:0000514

Axiom
annotated source: Chapman rearrangement
annotated property: definition
annotated target: Rearrangement of an aryl imino ether to yield an N,N-diaryl amide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Bergmann azlactone peptide synthesis
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has_part
  some values from: hydrolysis
definition: Reaction of an acetylated amino acid with an aldehyde then with a second amino acid, then hydrogenation and hydrolysis to form a dipeptide. It proceeds via an azlactone intermediate.
created by: batchelorc
creation date: 2014-03-10T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r38/
has_obo_namespace: RXNO
id: RXNO:0000515

Axiom
annotated source: Bergmann azlactone peptide synthesis
annotated property: definition
annotated target: Reaction of an acetylated amino acid with an aldehyde then with a second amino acid, then hydrogenation and hydrolysis to form a dipeptide. It proceeds via an azlactone intermediate.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Bergmann degradation
type: Class
subclass of: terminal amino-acid residue cleaving reaction
subclass of: Restriction
  on property: has specified product
  some values from: carboxamide
subclass of: Restriction
  on property: has specified reactant
  some values from: peptide
subclass of: Restriction
  on property: has_part
  some values from: hydrolysis
definition: Removal of a terminal amino acid residue from a peptide by benzoylation, azidation, treatment with benzyl alcohol, hydrogenation and hydrolysis.
created by: batchelorc
creation date: 2014-03-11T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r39/
has_obo_namespace: RXNO
id: RXNO:0000516

Axiom
annotated source: Bergmann degradation
annotated property: definition
annotated target: Removal of a terminal amino acid residue from a peptide by benzoylation, azidation, treatment with benzyl alcohol, hydrogenation and hydrolysis.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

terminal amino-acid residue cleaving reaction
type: Class
subclass of: cleaving reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: peptide
definition: Removal of a terminal amino acid residue from a peptide.
created by: batchelorc
creation date: 2014-03-11T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000517

Axiom
annotated source: terminal amino-acid residue cleaving reaction
annotated property: definition
annotated target: Removal of a terminal amino acid residue from a peptide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

acridine synthesis
type: Class
equivalent class: Class
  intersection of: molecular process
  intersection of: Restriction
    on property: has specified product
    some values from: acridines
subclass of: fused-ring-system formation
subclass of: azacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: acridines
definition: Ring formation reaction where the intended product is an acridine.
created by: batchelorc
creation date: 2014-03-12T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000518

Axiom
annotated source: acridine synthesis
annotated property: definition
annotated target: Ring formation reaction where the intended product is an acridine.
database_cross_reference: RSC:xp

Bernthsen acridine synthesis
type: Class
subclass of: acridine synthesis
subclass of: Restriction
  on property: has specified product
  some values from: acridines
definition: Reaction of a diarylamine in an organic acid or anhydride in the presence of zinc chloride to yield a 9-substituted acridine.
created by: batchelorc
creation date: 2014-03-12T09:00:00Z
database_cross_reference: doi:10.1039/b204243f
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r41/
has_exact_synonym: Bernthsen reaction
has_obo_namespace: RXNO
id: RXNO:0000519
comment: Definition source Merck Index, modified for errors.

Axiom
annotated source: Bernthsen acridine synthesis
annotated property: definition
annotated target: Reaction of a diarylamine in an organic acid or anhydride in the presence of zinc chloride to yield a 9-substituted acridine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

pyridine synthesis
type: Class
equivalent class: Class
  intersection of: molecular process
  intersection of: Restriction
    on property: has specified product
    some values from: pyridines
subclass of: azacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: pyridines
definition: Ring formation reaction where the intended product is a pyridine.
created by: batchelorc
creation date: 2014-03-12T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000520

Axiom
annotated source: pyridine synthesis
annotated property: definition
annotated target: Ring formation reaction where the intended product is a pyridine.
database_cross_reference: RSC:xp

carbazole synthesis
type: Class
equivalent class: Class
  intersection of: molecular process
  intersection of: Restriction
    on property: has specified product
    some values from: carbazoles
subclass of: fused-ring-system formation
subclass of: azacycle synthesis
subclass of: Restriction
  on property: has specified product
  some values from: carbazoles
definition: Ring formation reaction where the intended product is a carbazole.
created by: batchelorc
creation date: 2014-03-12T09:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000521

Axiom
annotated source: carbazole synthesis
annotated property: definition
annotated target: Ring formation reaction where the intended product is a carbazole.
database_cross_reference: RSC:xp

Betti reaction
type: Class
subclass of: molecular skeleton joining reaction
definition: Reaction of a phenol, an aromatic aldehyde and a primary aromatic or heterocyclic amine to yield a Betti's base, also known as an alpha-aminobenzylphenol.
created by: batchelorc
creation date: 2014-03-13T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r42/
has_exact_synonym: Betti synthesis
has_obo_namespace: RXNO
id: RXNO:0000522

Axiom
annotated source: Betti reaction
annotated property: definition
annotated target: Reaction of a phenol, an aromatic aldehyde and a primary aromatic or heterocyclic amine to yield a Betti's base, also known as an alpha-aminobenzylphenol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Bischler-Möhlau indole synthesis
type: Class
subclass of: indole synthesis
subclass of: Restriction
  on property: has specified product
  some values from: indoles
subclass of: Restriction
  on property: has specified reactant
  some values from: aromatic amine
definition: Reaction of a terminal hydroxyketone or terminal halogenoketone with an aromatic amine to yield a 2-substituted indole.
created by: batchelorc
creation date: 2014-03-13T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r45/
has_exact_synonym: Bischler reaction
has_exact_synonym: Bischler-Mohlau indole synthesis
has_exact_synonym: Bischler-Mohlau reaction
has_exact_synonym: Bischler-Möhlau reaction
has_obo_namespace: RXNO
id: RXNO:0000523
comment: Originally this involved a solvent but this need not be the case, see for example doi:10.1039/b719641e

Axiom
annotated source: Bischler-Möhlau indole synthesis
annotated property: definition
annotated target: Reaction of a terminal hydroxyketone or terminal halogenoketone with an aromatic amine to yield a 2-substituted indole.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Camps quinoline synthesis
type: Class
subclass of: quinoline synthesis
subclass of: Restriction
  on property: has specified product
  some values from: quinolines
definition: Cyclisation of an o-acylaminoacetophenone in alcoholic sodium hydroxide to form a substituted hydroxyquinoline.
created by: batchelorc
creation date: 2014-03-24T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r70/
has_exact_synonym: Camps cyclisation
has_exact_synonym: Camps cyclization
has_obo_namespace: RXNO
id: RXNO:0000524
comment: The substituent on the amino nitrogen can affect the ratio of 1-hydroxy to 3-hydroxy products.

Axiom
annotated source: Camps quinoline synthesis
annotated property: definition
annotated target: Cyclisation of an o-acylaminoacetophenone in alcoholic sodium hydroxide to form a substituted hydroxyquinoline.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Castro-Stephens coupling
type: Class
subclass of: molecular skeleton joining reaction
subclass of: palladium-catalysed carbon-carbon coupling reaction
subclass of: Restriction
  on property: has specified product
  some values from: arylacetylene
subclass of: Restriction
  on property: has_catalyst
  some values from: palladium atom
definition: Palladium-catalysed coupling of copper(I) acetylides with aryl halides to yield arylacetylenes.
created by: batchelorc
creation date: 2014-03-25T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r73/
has_obo_namespace: RXNO
id: RXNO:0000525

Axiom
annotated source: Castro-Stephens coupling
annotated property: definition
annotated target: Palladium-catalysed coupling of copper(I) acetylides with aryl halides to yield arylacetylenes.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Chichibabin pyridine synthesis
type: Class
subclass of: pyridine synthesis
subclass of: Restriction
  on property: has specified product
  some values from: pyridines
subclass of: Restriction
  on property: has specified reactant
  some values from: carbonyl compound
definition: Reaction of carbonyl compounds with ammonia or an amine to yield a pyridine.
created by: batchelorc
creation date: 2014-03-25T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r75/
has_obo_namespace: RXNO
id: RXNO:0000526

Axiom
annotated source: Chichibabin pyridine synthesis
annotated property: definition
annotated target: Reaction of carbonyl compounds with ammonia or an amine to yield a pyridine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Chichibabin reaction
type: Class
subclass of: amination
subclass of: substitution step
definition: Reaction of an azacycle with an alkali-metal amide to yield an aminated azacycle.
created by: batchelorc
creation date: 2014-03-25T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r76/
has_obo_namespace: RXNO
id: RXNO:0000527

Axiom
annotated source: Chichibabin reaction
annotated property: definition
annotated target: Reaction of an azacycle with an alkali-metal amide to yield an aminated azacycle.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Bodroux reaction
type: Class
subclass of: functional group modification
subclass of: Restriction
  on property: has specified reactant
  some values from: carboxylic ester
definition: Reaction of a carboxylic ester with a magnesium iodide alkylamide to yield a carboxamide.
created by: batchelorc
creation date: 2014-03-27T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r52/
has_obo_namespace: RXNO
id: RXNO:0000528

Axiom
annotated source: Bodroux reaction
annotated property: definition
annotated target: Reaction of a carboxylic ester with a magnesium iodide alkylamide to yield a carboxamide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Bogert-Cook synthesis
type: Class
subclass of: fused-ring-system formation
definition: Condensation of beta-phenylethylmagnesium bromide with a cyclohexanone followed by cyclisation and dehydration in concentrated sulfuric acid to yield an octahydrophenanthrene.
created by: batchelorc
creation date: 2014-03-27T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r53/
has_obo_namespace: RXNO
id: RXNO:0000529

Axiom
annotated source: Bogert-Cook synthesis
annotated property: definition
annotated target: Condensation of beta-phenylethylmagnesium bromide with a cyclohexanone followed by cyclisation and dehydration in concentrated sulfuric acid to yield an octahydrophenanthrene.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Bohn-Schmidt reaction
type: Class
subclass of: functional group addition step
definition: Reaction of a hydroxylated anthraquinone with fuming sulfuric acid or sulfuric acid in boric acid in the presence of a mercury or selenium catalyst to form a more hydroxylated anthraquinone.
created by: batchelorc
creation date: 2014-03-27T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r54/
has_obo_namespace: RXNO
id: RXNO:0000530

Axiom
annotated source: Bohn-Schmidt reaction
annotated property: definition
annotated target: Reaction of a hydroxylated anthraquinone with fuming sulfuric acid or sulfuric acid in boric acid in the presence of a mercury or selenium catalyst to form a more hydroxylated anthraquinone.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Boord olefin synthesis
type: Class
subclass of: olefination
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
subclass of: Restriction
  on property: has_part
  some values from: elimination reaction
subclass of: Restriction
  on property: has_part
  some values from: Grignard reaction
definition: Etherification of an aldehyde followed by bromination and reaction with a Grignard reagent followed by treatment with zinc to eliminate the halogen and alkoxy groups to produce an olefin.
created by: batchelorc
creation date: 2014-03-27T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r55/
has_obo_namespace: RXNO
id: RXNO:0000531

Axiom
annotated source: Boord olefin synthesis
annotated property: definition
annotated target: Etherification of an aldehyde followed by bromination and reaction with a Grignard reagent followed by treatment with zinc to eliminate the halogen and alkoxy groups to produce an olefin.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Borsche-Drechsel cyclisation
type: Class
subclass of: carbazole synthesis
subclass of: Restriction
  on property: has specified product
  some values from: carbazoles
definition: Rearrangement of a cyclohexanone phenylhydrazone followed by oxidation to yield a carbazole.
created by: batchelorc
creation date: 2014-03-27T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r56/
has_exact_synonym: Borsche-Drechsel carbazole synthesis
has_exact_synonym: Borsche-Drechsel cyclization
has_obo_namespace: RXNO
id: RXNO:0000532

Axiom
annotated source: Borsche-Drechsel cyclisation
annotated property: definition
annotated target: Rearrangement of a cyclohexanone phenylhydrazone followed by oxidation to yield a carbazole.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Bouveault aldehyde synthesis
type: Class
subclass of: chain lengthening
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: organolithium compound
subclass of: Restriction
  on property: has specified reactant
  some values from: organomagnesium halide
definition: Reaction of an organomagnesium or organolithium compound with an N,N'-disubstituted formamide to yield the next homologous aldehyde.
created by: batchelorc
creation date: 2014-03-27T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r57/
has_obo_namespace: RXNO
id: RXNO:0000533

Axiom
annotated source: Bouveault aldehyde synthesis
annotated property: definition
annotated target: Reaction of an organomagnesium or organolithium compound with an N,N'-disubstituted formamide to yield the next homologous aldehyde.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Bradsher cyclisation
type: Class
subclass of: fused-ring-system formation
definition: Diels-Alder reaction of a dienophile with a cationic aromatic azadiene to yield a bridged-ring system.
created by: batchelorc
creation date: 2014-03-27T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r60/
has_exact_synonym: Bradsher cyclization
has_exact_synonym: Bradsher cycloaddition
has_obo_namespace: RXNO
id: RXNO:0000534

Axiom
annotated source: Bradsher cyclisation
annotated property: definition
annotated target: Diels-Alder reaction of a dienophile with a cationic aromatic azadiene to yield a bridged-ring system.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Bradsher reaction
type: Class
subclass of: fused-ring-system formation
definition: Reaction of an ortho-acyldiarylmethane, catalysed by acid, to yield an anthracene.
created by: batchelorc
creation date: 2014-04-08T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r61/
has_obo_namespace: RXNO
id: RXNO:0000535

Axiom
annotated source: Bradsher reaction
annotated property: definition
annotated target: Reaction of an ortho-acyldiarylmethane, catalysed by acid, to yield an anthracene.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Parham cyclisation
type: Class
subclass of: fused-ring-system formation
subclass of: Restriction
  on property: has specified reactant
  some values from: bromoarene
definition: Reaction of a bromoarene that has an electrophilic group at the para-position with lithium bromide or lithium iodide followed by intramolecular cyclisation to yield a fused-ring system.
created by: batchelorc
creation date: 2014-04-08T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r317/
has_obo_namespace: RXNO
id: RXNO:0000536

Axiom
annotated source: Parham cyclisation
annotated property: definition
annotated target: Reaction of a bromoarene that has an electrophilic group at the para-position with lithium bromide or lithium iodide followed by intramolecular cyclisation to yield a fused-ring system.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Quelet reaction
type: Class
subclass of: functional group addition step
definition: Reaction of an aliphatic aldehyde with a phenolic ether and hydrochloric acid to yield an alpha-chloroalkylphenolic ether.
created by: batchelorc
creation date: 2014-04-14T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r357/
has_obo_namespace: RXNO
id: RXNO:0000537

Axiom
annotated source: Quelet reaction
annotated property: definition
annotated target: Reaction of an aliphatic aldehyde with a phenolic ether and hydrochloric acid to yield an alpha-chloroalkylphenolic ether.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Chugaev reaction
type: Class
subclass of: molecular skeleton elimination reaction
subclass of: Restriction
  on property: has specified product
  some values from: olefin
definition: Elimination of a water molecule from a secondary alcohol to yield an olefin.
created by: batchelorc
creation date: 2014-04-14T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r77/
has_obo_namespace: RXNO
id: RXNO:0000538

Axiom
annotated source: Chugaev reaction
annotated property: definition
annotated target: Elimination of a water molecule from a secondary alcohol to yield an olefin.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Cope elimination
type: Class
subclass of: molecular skeleton elimination reaction
subclass of: Restriction
  on property: has specified product
  some values from: olefin
definition: Elimination of a hydroxylamine from an amine oxide by pyrolysis to yield an olefin.
created by: batchelorc
creation date: 2014-04-14T09:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r85/
database_cross_reference: https://www.wikidata.org/wiki/Q900370
has_exact_synonym: Cope reaction
has_obo_namespace: RXNO
id: RXNO:0000539

Axiom
annotated source: Cope elimination
annotated property: definition
annotated target: Elimination of a hydroxylamine from an amine oxide by pyrolysis to yield an olefin.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Sugasawa reaction
type: Class
subclass of: functional group addition step
definition: Reaction of an aniline with a nitrile in the presence of boron trichloride and a Lewis acid to yield an ortho-acylated aniline.
created by: batchelorc
creation date: 2014-04-14T13:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r423/
has_obo_namespace: RXNO
id: RXNO:0000540

Axiom
annotated source: Sugasawa reaction
annotated property: definition
annotated target: Reaction of an aniline with a nitrile in the presence of boron trichloride and a Lewis acid to yield an ortho-acylated aniline.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

palladium-catalysed Kumada coupling
type: Class
subclass of: Kumada coupling
subclass of: palladium-catalysed carbon-carbon coupling reaction
subclass of: Restriction
  on property: has_catalyst
  some values from: palladium atom
definition: A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a palladium catalyst.
created by: batchelorc
creation date: 2014-04-14T13:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000541

Axiom
annotated source: palladium-catalysed Kumada coupling
annotated property: definition
annotated target: A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a palladium catalyst.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

nickel-catalysed Kumada coupling
type: Class
subclass of: Kumada coupling
subclass of: Restriction
  on property: has_catalyst
  some values from: nickel atom
definition: A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a nickel catalyst.
created by: batchelorc
creation date: 2014-04-14T13:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000542

Axiom
annotated source: nickel-catalysed Kumada coupling
annotated property: definition
annotated target: A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a nickel catalyst.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429
database_cross_reference: https://orcid.org/0000-0002-4077-4719

Eastwood reaction
type: Class
subclass of: molecular skeleton elimination reaction
subclass of: Restriction
  on property: has specified product
  some values from: olefin
definition: Reaction of a 1,2-diol with triethoxymethane under heat to yield an olefin.
created by: batchelorc
creation date: 2014-04-15T11:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r121/
has_obo_namespace: RXNO
id: RXNO:0000543
comment: The reaction is stereospecific. It proceeds via a 1,3-dioxolane intermediate.

Axiom
annotated source: Eastwood reaction
annotated property: definition
annotated target: Reaction of a 1,2-diol with triethoxymethane under heat to yield an olefin.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Saegusa oxidation
type: Class
subclass of: molecular skeleton elimination reaction
definition: Reaction of silyl enol ethers with palladium acetate in acetonitrile to yield an alpha,beta-unsaturated ketone.
created by: batchelorc
creation date: 2014-04-22T16:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r382/
has_obo_namespace: RXNO
id: RXNO:0000544

Axiom
annotated source: Saegusa oxidation
annotated property: definition
annotated target: Reaction of silyl enol ethers with palladium acetate in acetonitrile to yield an alpha,beta-unsaturated ketone.
database_cross_reference: doi:10.1021/jo00399a052

Sandmeyer diphenylurea isatin synthesis
type: Class
subclass of: indole synthesis
subclass of: Restriction
  on property: has specified product
  some values from: isatin
subclass of: Restriction
  on property: has_part
  some values from: hydrolysis
definition: Reaction of diphenylthiourea with lead carbonate and potassium cyanide to form a cyanoformidine followed by ring closure and acid hydrolysis to yield isatin.
created by: batchelorc
creation date: 2014-04-24T15:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r384/
has_obo_namespace: RXNO
id: RXNO:0000545

Axiom
annotated source: Sandmeyer diphenylurea isatin synthesis
annotated property: definition
annotated target: Reaction of diphenylthiourea with lead carbonate and potassium cyanide to form a cyanoformidine followed by ring closure and acid hydrolysis to yield isatin.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Sandmeyer isonitrosoacetanilide isatin synthesis
type: Class
subclass of: indole synthesis
subclass of: Restriction
  on property: has specified product
  some values from: isatin
subclass of: Restriction
  on property: has_part
  some values from: hydrolysis
definition: Reaction of aniline, hydroxylamine and chloral hydrate to form an aniline intermediate followed by cyclization in acid and hydrolysis to yield isatin.
created by: batchelorc
creation date: 2014-04-24T15:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r385/
has_obo_namespace: RXNO
id: RXNO:0000546

Axiom
annotated source: Sandmeyer isonitrosoacetanilide isatin synthesis
annotated property: definition
annotated target: Reaction of aniline, hydroxylamine and chloral hydrate to form an aniline intermediate followed by cyclization in acid and hydrolysis to yield isatin.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Sarett oxidation
type: Class
equivalent class: Class
  union of: Sarett primary alcohol oxidation
  union of: Sarett secondary alcohol oxidation
subclass of: alcohol oxidation
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified reactant
  some values from: chromium trioxide
definition: Oxidation of an alcohol with a pyridine-chromium trioxide complex to yield a carbonyl compound.
created by: batchelorc
creation date: 2014-04-24T15:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r387/
has_obo_namespace: RXNO
id: RXNO:0000547

Axiom
annotated source: Sarett oxidation
annotated property: definition
annotated target: Oxidation of an alcohol with a pyridine-chromium trioxide complex to yield a carbonyl compound.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Sarett primary alcohol oxidation
type: Class
subclass of: primary alcohol oxidation to aldehyde
subclass of: Sarett oxidation
definition: Oxidation of a primary alcohol with a pyridine-chromium trioxide complex to yield an aldehyde.
created by: batchelorc
creation date: 2014-04-24T15:00:00Z
database_cross_reference: https://www.wikidata.org/wiki/Q2227511
has_obo_namespace: RXNO
id: RXNO:0000548

Axiom
annotated source: Sarett primary alcohol oxidation
annotated property: definition
annotated target: Oxidation of a primary alcohol with a pyridine-chromium trioxide complex to yield an aldehyde.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Sarett secondary alcohol oxidation
type: Class
subclass of: secondary alcohol oxidation to ketone
subclass of: Sarett oxidation
definition: Oxidation of a secondary alcohol with a pyridine-chromium trioxide complex to yield a ketone.
created by: batchelorc
creation date: 2014-04-24T15:00:00Z
has_obo_namespace: RXNO
id: RXNO:0000549

Axiom
annotated source: Sarett secondary alcohol oxidation
annotated property: definition
annotated target: Oxidation of a secondary alcohol with a pyridine-chromium trioxide complex to yield a ketone.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Collins oxidation
type: Class
subclass of: alcohol oxidation
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified reactant
  some values from: chromium trioxide
definition: Oxidation of a primary alcohol with a pyridine-chromium trioxide complex in dichloromethane to yield an aldehyde.
created by: batchelorc
creation date: 2014-04-24T15:00:00Z
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r387/
has_obo_namespace: RXNO
id: RXNO:0000550

Axiom
annotated source: Collins oxidation
annotated property: definition
annotated target: Oxidation of a primary alcohol with a pyridine-chromium trioxide complex in dichloromethane to yield an aldehyde.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

reductive imination
type: Class
subclass of: imination
subclass of: functional group modification
definition: A functional group modification where a carbonyl oxygen is replaced by an imine.
has_obo_namespace: RXNO
id: RXNO:0000551

Axiom
annotated source: reductive imination
annotated property: definition
annotated target: A functional group modification where a carbonyl oxygen is replaced by an imine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Leuckart aldehyde reaction
type: Class
subclass of: Leuckart reaction
subclass of: Restriction
  on property: has participant ceasing to exist
  some values from: aldehyde
definition: Reductive amination of an aldehyde with ammonium formate or formamide to form an amine.
has_obo_namespace: RXNO
id: RXNO:0000552

Axiom
annotated source: Leuckart aldehyde reaction
annotated property: definition
annotated target: Reductive amination of an aldehyde with ammonium formate or formamide to form an amine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Leuckart ketone reaction
type: Class
subclass of: Leuckart reaction
subclass of: Restriction
  on property: has participant ceasing to exist
  some values from: ketone
definition: Reductive amination of a ketone with ammonium formate or formamide to form an amine.
has_obo_namespace: RXNO
id: RXNO:0000553

Axiom
annotated source: Leuckart ketone reaction
annotated property: definition
annotated target: Reductive amination of a ketone with ammonium formate or formamide to form an amine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Appel bromination with tetrabromomethane
type: Class
subclass of: Appel bromination
subclass of: Restriction
  on property: has specified reactant
  some values from: tetrabromomethane
definition: Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane.
has_obo_namespace: RXNO
id: RXNO:0000554

Axiom
annotated source: Appel bromination with tetrabromomethane
annotated property: definition
annotated target: Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Appel bromination with bromine
type: Class
subclass of: Appel bromination
subclass of: Restriction
  on property: has specified reactant
  some values from: dibromine
definition: Conversion of an alcohol to an alkyl bromide with triphenylphosphine and bromine.
has_obo_namespace: RXNO
id: RXNO:0000555

Axiom
annotated source: Appel bromination with bromine
annotated property: definition
annotated target: Conversion of an alcohol to an alkyl bromide with triphenylphosphine and bromine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Corey-Fuchs terminal dibromoolefination
type: Class
subclass of: olefination
subclass of: Restriction
  on property: has specified reactant
  some values from: triphenylphosphane oxide
subclass of: Restriction
  on property: has specified reactant
  some values from: tetrabromomethane
definition: Reaction of an aldehyde with tetrabromomethane and triphenylphosphine to yield a terminal dibromoolefin.
has_narrow_synonym: Corey-Fuchs reaction step 1
has_obo_namespace: RXNO
id: RXNO:0000556
comment: This is the first step of the Corey-Fuchs reaction. The second step is the Fritsch-Buttenberg-Wiechell rearrangement.

Axiom
annotated source: Corey-Fuchs terminal dibromoolefination
annotated property: definition
annotated target: Reaction of an aldehyde with tetrabromomethane and triphenylphosphine to yield a terminal dibromoolefin.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

obsolete: Heck-type reaction/cross-coupling
type: Class
has_obo_namespace: RXNO
id: RXNO:0000557
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000624 for Heck-type reaction and RXNO:0000603 for cross-coupling.
deprecated: true

obsolete: bromo Heck reaction/Liebeskind-Srogl coupling
type: Class
has_obo_namespace: RXNO
id: RXNO:0000558
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000625 for the bromo Heck reaction and RXNO:0000604 for Liebeskind-Srogl coupling.
deprecated: true

obsolete: chloro Heck reaction/Fukuyama coupling
type: Class
has_obo_namespace: RXNO
id: RXNO:0000559
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000626 for the chloro Heck reaction and RXNO:0000605 for Fukuyama coupling.
deprecated: true

obsolete: iodo Heck reaction/chloride Finkelstein reaction
type: Class
has_obo_namespace: RXNO
id: RXNO:0000560
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000627 for the iodo Heck reaction and RXNO:0000606 for the chloride Finkelstein reaction.
deprecated: true

obsolete: triflyloxy Heck reaction/bromide Finkelstein reaction
type: Class
has_obo_namespace: RXNO
id: RXNO:0000561
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000628 for the triflyloxy Heck reaction and RXNO:0000607 for the bromide Finkelstein reaction.
deprecated: true

obsolete: bromo Heck-type reaction/sulfonate ester Finkelstein reaction
type: Class
has_obo_namespace: RXNO
id: RXNO:0000562
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000629 for the bromo Heck-type reaction and RXNO:0000608 for the sulfonate ester Finkelstein reaction.
deprecated: true

obsolete: chloro Heck-type reaction/Sandmeyer fluorination
type: Class
has_obo_namespace: RXNO
id: RXNO:0000563
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000630 for the chloro Heck-type reaction and RXNO:0000609 for Sandmeyer fluorination.
deprecated: true

obsolete: acyclic Beckmann rearrangement/Sandmeyer chlorination
type: Class
has_obo_namespace: RXNO
id: RXNO:0000564
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000631 for acyclic Beckmann rearrangement and RXNO:0000610 for Sandmeyer chlorination.
deprecated: true

obsolete: Baeyer–Emmerling indole synthesis/Sandmeyer bromination
type: Class
has_obo_namespace: RXNO
id: RXNO:0000565
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000632 for Baeyer-Emmerling indole synthesis and RXNO:0000611 for Sandmeyer bromination.
deprecated: true

obsolete: bromo Sonogashira coupling/Sandmeyer iodination
type: Class
has_obo_namespace: RXNO
id: RXNO:0000566
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000633 for bromo Sonogashira coupling and RXNO:0000612 for Sandmeyer iodination.
deprecated: true

obsolete: bromo Suzuki coupling/iodo Heck reaction
type: Class
has_obo_namespace: RXNO
id: RXNO:0000567
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000634 for bromo Suzuki coupling and RXNO:0000613 for the iodo Heck reaction.
deprecated: true

obsolete: bromo Suzuki-type coupling/triflyloxy Heck reaction
type: Class
has_obo_namespace: RXNO
id: RXNO:0000568
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000635 for bromo Suzuki-type coupling and RXNO:0000628 for the triflyloxy Heck reaction.
deprecated: true

obsolete: bromolactonization/bromo Heck-type reaction
type: Class
has_obo_namespace: RXNO
id: RXNO:0000569
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000636 for bromolactonization and RXNO:0000629 for the bromo Heck-type reaction.
deprecated: true

obsolete: chloro Sonogashira coupling/chloro Heck-type reaction
type: Class
has_obo_namespace: RXNO
id: RXNO:0000570
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000637 for chloro Sonogashira coupling and RXNO:0000630 for the chloro Heck-type reaction.
deprecated: true

obsolete: chloro Suzuki coupling/Heck-type reaction
type: Class
has_obo_namespace: RXNO
id: RXNO:0000571
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000638 for chloro Suzuki coupling and RXNO:0000624 for the Heck-type reaction.
deprecated: true

obsolete: chloro Suzuki-type coupling/bromo Heck reaction
type: Class
has_obo_namespace: RXNO
id: RXNO:0000572
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000639 for chloro Suzuki-type coupling and RXNO:0000625 for the bromo Heck reaction.
deprecated: true

obsolete: chlorolactonization/chloro Heck reaction
type: Class
has_obo_namespace: RXNO
id: RXNO:0000573
comment: This term has been obsoleted because the ID was inadvertently reused for two classes. See RXNO:0000640 for chlorolactonization and RXNO:0000626 for the chloro Heck reaction.
deprecated: true

cyclic Beckmann rearrangement
type: Class
subclass of: Beckmann rearrangement
subclass of: azacycle synthesis
definition: A Beckmann rearrangement which produces a cyclic product.
database_cross_reference: NAMERXN:4.1.6
has_obo_namespace: RXNO
id: RXNO:0000574

Axiom
annotated source: cyclic Beckmann rearrangement
annotated property: definition
annotated target: A Beckmann rearrangement which produces a cyclic product.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Dess-Martin aldehyde oxidation
type: Class
subclass of: Dess-Martin oxidation
definition: A Dess-Martin oxidation of a primary alcohol to an aldehyde.
database_cross_reference: NAMERXN:8.1.2
has_exact_synonym: aldehyde Dess-Martin oxidation
has_obo_namespace: RXNO
id: RXNO:0000575

Axiom
annotated source: Dess-Martin aldehyde oxidation
annotated property: definition
annotated target: A Dess-Martin oxidation of a primary alcohol to an aldehyde.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Dess-Martin ketone oxidation
type: Class
subclass of: Dess-Martin oxidation
definition: A Dess-Martin oxidation of a secondary alcohol to a ketone.
database_cross_reference: NAMERXN:8.1.3
has_exact_synonym: ketone Dess-Martin oxidation
has_obo_namespace: RXNO
id: RXNO:0000576

Axiom
annotated source: Dess-Martin ketone oxidation
annotated property: definition
annotated target: A Dess-Martin oxidation of a secondary alcohol to a ketone.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Friedlander quinoline synthesis
type: Class
subclass of: quinoline synthesis
definition: Synthesis of a quinoline by reaction of a 2-aminobenzaldehyde with a ketone.
database_cross_reference: NAMERXN:4.1.29
database_cross_reference: https://www.wikidata.org/wiki/Q1058388
has_exact_synonym: Friedlaender synthesis
has_exact_synonym: Friedlander synthesis
has_exact_synonym: Friedländer synthesis
has_obo_namespace: RXNO
id: RXNO:0000577

Axiom
annotated source: Friedlander quinoline synthesis
annotated property: definition
annotated target: Synthesis of a quinoline by reaction of a 2-aminobenzaldehyde with a ketone.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Gewald reaction
type: Class
subclass of: thiacycle synthesis
definition: Reaction of an aldehyde or ketone with an alpha-cyanoester to form a 2-aminothiophene.
database_cross_reference: NAMERXN:4.3.4
database_cross_reference: https://www.wikidata.org/wiki/Q240091
has_exact_synonym: Gewald thiophene synthesis
has_obo_namespace: RXNO
id: RXNO:0000578

Axiom
annotated source: Gewald reaction
annotated property: definition
annotated target: Reaction of an aldehyde or ketone with an alpha-cyanoester to form a 2-aminothiophene.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

iodo Sonogashira coupling
type: Class
subclass of: Sonogashira coupling
definition: A Sonogashira coupling where the aryl halide is an aryl iodide.
database_cross_reference: NAMERXN:3.3.4
has_obo_namespace: RXNO
id: RXNO:0000579

Axiom
annotated source: iodo Sonogashira coupling
annotated property: definition
annotated target: A Sonogashira coupling where the aryl halide is an aryl iodide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

iodo Suzuki coupling
type: Class
subclass of: Suzuki-Miyaura coupling
definition: A Suzuki coupling where the halide is an iodide.
database_cross_reference: NAMERXN:3.1.3
has_exact_synonym: iodo Suzuki-Miyaura coupling
has_obo_namespace: RXNO
id: RXNO:0000580

Axiom
annotated source: iodo Suzuki coupling
annotated property: definition
annotated target: A Suzuki coupling where the halide is an iodide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

iodo Suzuki-type coupling
type: Class
subclass of: Suzuki-type coupling
definition: A Suzuki-type coupling where the halide is an iodide.
database_cross_reference: NAMERXN:3.1.7
has_exact_synonym: iodo Suzuki-Miyaura-type coupling
has_obo_namespace: RXNO
id: RXNO:0000581

Axiom
annotated source: iodo Suzuki-type coupling
annotated property: definition
annotated target: A Suzuki-type coupling where the halide is an iodide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

iodolactonization
type: Class
subclass of: halolactonization
definition: A halolactionization where the halide is an iodide.
database_cross_reference: NAMERXN:4.2.15
database_cross_reference: https://www.wikidata.org/wiki/Q6062283
has_exact_synonym: iodolactonisation
has_obo_namespace: RXNO
id: RXNO:0000582

Axiom
annotated source: iodolactonization
annotated property: definition
annotated target: A halolactionization where the halide is an iodide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Niementowski quinazoline synthesis
type: Class
subclass of: azacycle synthesis
subclass of: Restriction
  on property: has specified reactant
  some values from: arenecarbaldehyde
definition: An azacycle synthesis where the product is a 4-oxo-3,4-dihydroquinazoline and the reactants are a 2-aminobenzoic acid and an amide.
database_cross_reference: NAMERXN:4.1.30
database_cross_reference: https://www.wikidata.org/wiki/Q1059542
has_obo_namespace: RXNO
id: RXNO:0000583

Axiom
annotated source: Niementowski quinazoline synthesis
annotated property: definition
annotated target: An azacycle synthesis where the product is a 4-oxo-3,4-dihydroquinazoline and the reactants are a 2-aminobenzoic acid and an amide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Niementowski quinoline synthesis
type: Class
subclass of: quinoline synthesis
definition: A quinoline synthesis where the product is a gamma-hydroxyquinoline and the reactants are a 2-aminobenzoic acid and an aldehyde or ketone.
database_cross_reference: NAMERXN:4.1.31
database_cross_reference: https://www.wikidata.org/wiki/Q2733837
has_obo_namespace: RXNO
id: RXNO:0000584

Axiom
annotated source: Niementowski quinoline synthesis
annotated property: definition
annotated target: A quinoline synthesis where the product is a gamma-hydroxyquinoline and the reactants are a 2-aminobenzoic acid and an aldehyde or ketone.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Pomeranz–Fritsch reaction
type: Class
subclass of: azacycle synthesis
definition: An azacycle synthesis where the product is an isoquinoline and the reactants are a benzaldehyde and a 2,2-dialkoxyethylamine.
database_cross_reference: NAMERXN:4.1.65
database_cross_reference: https://www.wikidata.org/wiki/Q18217151
has_exact_synonym: Pomeranz–Fritsch cyclization
has_exact_synonym: Pomeranz–Fritsch isoquinoline synthesis
has_obo_namespace: RXNO
id: RXNO:0000585

Axiom
annotated source: Pomeranz–Fritsch reaction
annotated property: definition
annotated target: An azacycle synthesis where the product is an isoquinoline and the reactants are a benzaldehyde and a 2,2-dialkoxyethylamine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Steglich esterification
type: Class
subclass of: O-acylation to ester
definition: An O-acylation to ester where dicyclohexylcarbodiimide is used as a coupling reagent and 4-dimethylaminopyridine as a catalyst.
database_cross_reference: NAMERXN:2.6.9
database_cross_reference: https://www.wikidata.org/wiki/Q695687
has_obo_namespace: RXNO
id: RXNO:0000586

Axiom
annotated source: Steglich esterification
annotated property: definition
annotated target: An O-acylation to ester where dicyclohexylcarbodiimide is used as a coupling reagent and 4-dimethylaminopyridine as a catalyst.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

triflyloxy Sonogashira coupling
type: Class
subclass of: Sonogashira coupling
definition: A Sonogashira coupling where the role of the halide is played by a triflyloxy group.
database_cross_reference: NAMERXN:3.3.5
has_exact_synonym: Triflyloxy Sonogashira coupling
has_obo_namespace: RXNO
id: RXNO:0000587

Axiom
annotated source: triflyloxy Sonogashira coupling
annotated property: definition
annotated target: A Sonogashira coupling where the role of the halide is played by a triflyloxy group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

triflyloxy Suzuki coupling
type: Class
subclass of: Suzuki-Miyaura coupling
subclass of: triflyloxy Suzuki-type coupling
definition: A Suzuki coupling where the rule of the halide is played by a triflyloxy group.
database_cross_reference: NAMERXN:3.1.4
has_exact_synonym: Triflyloxy Suzuki coupling
has_exact_synonym: triflyloxy Suzuki-Miyaura coupling
has_obo_namespace: RXNO
id: RXNO:0000588

Axiom
annotated source: triflyloxy Suzuki coupling
annotated property: definition
annotated target: A Suzuki coupling where the rule of the halide is played by a triflyloxy group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

triflyloxy Suzuki-type coupling
type: Class
subclass of: Suzuki-type coupling
definition: A Suzuki-type coupling where the rule of the halide is played by a triflyloxy group.
database_cross_reference: NAMERXN:3.1.8
has_exact_synonym: Triflyloxy Suzuki-type coupling
has_exact_synonym: triflyloxy Suzuki-Miyaura-type coupling
has_obo_namespace: RXNO
id: RXNO:0000589

Axiom
annotated source: triflyloxy Suzuki-type coupling
annotated property: definition
annotated target: A Suzuki-type coupling where the rule of the halide is played by a triflyloxy group.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Wenker synthesis
type: Class
subclass of: molecular dehydration reaction
subclass of: azacycle synthesis
definition: Synthesis of an aziridine by dehydrating a beta aminoalcohol with sulfuric acid.
database_cross_reference: NAMERXN:4.1.66
database_cross_reference: https://doi.org/10.1021/ja01314a504
database_cross_reference: https://www.wikidata.org/wiki/Q900233
has_exact_synonym: Wenker aziridine synthesis
has_obo_namespace: RXNO
id: RXNO:0000590

Axiom
annotated source: Wenker synthesis
annotated property: definition
annotated target: Synthesis of an aziridine by dehydrating a beta aminoalcohol with sulfuric acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Hinsberg thiophene synthesis
type: Class
subclass of: thiacycle synthesis
definition: Reaction of an alpha-diketone with a dialkyl thiodiacetate to form a thiophene dicarboxylic acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r202/
database_cross_reference: https://www.wikidata.org/wiki/Q18020904
has_obo_namespace: RXNO
id: RXNO:0000591

Axiom
annotated source: Hinsberg thiophene synthesis
annotated property: definition
annotated target: Reaction of an alpha-diketone with a dialkyl thiodiacetate to form a thiophene dicarboxylic acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Suzuki-type coupling
type: Class
subclass of: carbon-carbon coupling reaction
definition: The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate.
has_obo_namespace: RXNO
id: RXNO:0000592

Axiom
annotated source: Suzuki-type coupling
annotated property: definition
annotated target: The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

halolactonization
type: Class
subclass of: oxacycle synthesis
definition: Addition of a carboxylic acid oxygen and halogen across a carbon-carbon double bond to form a lactone.
has_exact_synonym: halolactonisation
has_obo_namespace: RXNO
id: RXNO:0000593

Axiom
annotated source: halolactonization
annotated property: definition
annotated target: Addition of a carboxylic acid oxygen and halogen across a carbon-carbon double bond to form a lactone.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Ciamician-Dennstedt rearrangement
type: Class
subclass of: ring expansion
definition: Expansion of a pyrrole ring by heating with a halogeno compond to form a 3-halogenopyridine.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r78/
database_cross_reference: https://www.wikidata.org/wiki/Q6151790
has_obo_namespace: RXNO
id: RXNO:0000594

Axiom
annotated source: Ciamician-Dennstedt rearrangement
annotated property: definition
annotated target: Expansion of a pyrrole ring by heating with a halogeno compond to form a 3-halogenopyridine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Claisen-Schmidt condensation
type: Class
subclass of: molecular dehydration reaction
definition: Condensation of an aromatic aldehyde with an aliphatic aldehyde or ketone in the presence of a relatively strong base to from an alpha,beta-unsaturated aldehyde or ketone.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r81/
database_cross_reference: https://www.wikidata.org/wiki/Q56298266
has_obo_namespace: RXNO
id: RXNO:0000595

Axiom
annotated source: Claisen-Schmidt condensation
annotated property: definition
annotated target: Condensation of an aromatic aldehyde with an aliphatic aldehyde or ketone in the presence of a relatively strong base to from an alpha,beta-unsaturated aldehyde or ketone.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

obsolete: Combes quinoline synthesis/Conrad%E2%80%93Limpach_synthesis
type: Class
has_obo_namespace: RXNO
id: RXNO:0000596
comment: this ID has been obsoleted because it was used for two different classes.
deprecated: true

Corey-Bakshi-Shibata reduction
type: Class
subclass of: ketone reduction
subclass of: functional group reduction
definition: Enantioselective reduction of a ketone to an alcohol with a chiral oxazaborolidine.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r87/
database_cross_reference: https://www.wikidata.org/wiki/Q903598
has_exact_synonym: CBS reduction
has_exact_synonym: Corey-Itsuno reduction
has_obo_namespace: RXNO
id: RXNO:0000597

Axiom
annotated source: Corey-Bakshi-Shibata reduction
annotated property: definition
annotated target: Enantioselective reduction of a ketone to an alcohol with a chiral oxazaborolidine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Johnson-Corey-Chaykovsky reaction
type: Class
equivalent class: Class
  union of: Johnson-Corey-Chaykovsky epoxide synthesis
  union of: Johnson-Corey-Chaykovsky cyclopropane synthesis
  union of: Johnson-Corey-Chaykovsky aziridine synthesis
  union of: Johnson-Corey-Chaykovsky thiirane synthesis
subclass of: ring formation reaction step
definition: Reaction of a sulfur ylide with a double-bond to produce a three-membered ring.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r88/
database_cross_reference: https://www.wikidata.org/wiki/Q1582682
has_exact_synonym: Corey-Chaykovsky reaction
has_obo_namespace: RXNO
id: RXNO:0000598

Axiom
annotated source: Johnson-Corey-Chaykovsky reaction
annotated property: definition
annotated target: Reaction of a sulfur ylide with a double-bond to produce a three-membered ring.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Johnson-Corey-Chaykovsky epoxide synthesis
type: Class
subclass of: oxacycle synthesis
definition: Reaction of a sulfur ylide with a ketone to produce an epoxide.
has_obo_namespace: RXNO
id: RXNO:0000599

Axiom
annotated source: Johnson-Corey-Chaykovsky epoxide synthesis
annotated property: definition
annotated target: Reaction of a sulfur ylide with a ketone to produce an epoxide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Johnson-Corey-Chaykovsky cyclopropane synthesis
type: Class
subclass of: Johnson-Corey-Chaykovsky reaction
definition: Reaction of a sulfur ylide with an olefin to produce a cyclopropane.
has_obo_namespace: RXNO
id: RXNO:0000600

Axiom
annotated source: Johnson-Corey-Chaykovsky cyclopropane synthesis
annotated property: definition
annotated target: Reaction of a sulfur ylide with an olefin to produce a cyclopropane.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Johnson-Corey-Chaykovsky aziridine synthesis
type: Class
subclass of: azacycle synthesis
definition: Reaction of a sulfur ylide with an imine to produce an aziridine.
has_obo_namespace: RXNO
id: RXNO:0000601

Axiom
annotated source: Johnson-Corey-Chaykovsky aziridine synthesis
annotated property: definition
annotated target: Reaction of a sulfur ylide with an imine to produce an aziridine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Johnson-Corey-Chaykovsky thiirane synthesis
type: Class
subclass of: thiacycle synthesis
definition: Reaction of a sulfur ylide with a thione to produce a thiirane.
has_obo_namespace: RXNO
id: RXNO:0000602

Axiom
annotated source: Johnson-Corey-Chaykovsky thiirane synthesis
annotated property: definition
annotated target: Reaction of a sulfur ylide with a thione to produce a thiirane.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

cross-coupling
type: Class
subclass of: molecular skeleton joining reaction
definition: A joining reaction where a carbon-carbon bond is formed between unlike moieties.
database_cross_reference: https://www.wikidata.org/wiki/Q7127709
has_obo_namespace: RXNO
id: RXNO:0000603

Axiom
annotated source: cross-coupling
annotated property: definition
annotated target: A joining reaction where a carbon-carbon bond is formed between unlike moieties.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Liebeskind-Srogl coupling
type: Class
subclass of: cross-coupling
subclass of: Class
  intersection of: Restriction
    on property: has specified reactant
    some values from: boronic acids
  intersection of: Restriction
    on property: has specified reactant
    some values from: thioester
subclass of: Restriction
  on property: has specified product
  some values from: ketone
subclass of: Restriction
  on property: has_catalyst
  some values from: transition element atom
definition: A cross-coupling reaction where a thioester and a boronic acid react to form a ketone. It uses a metal catalyst.
database_cross_reference: https://www.wikidata.org/wiki/Q6543886
has_obo_namespace: RXNO
id: RXNO:0000604

Axiom
annotated source: Liebeskind-Srogl coupling
annotated property: definition
annotated target: A cross-coupling reaction where a thioester and a boronic acid react to form a ketone. It uses a metal catalyst.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Fukuyama coupling
type: Class
subclass of: cross-coupling
subclass of: Class
  intersection of: Restriction
    on property: has specified reactant
    some values from: thioester
  intersection of: Restriction
    on property: has specified reactant
    some values from: organozinc compound
subclass of: Restriction
  on property: has specified product
  some values from: ketone
subclass of: Restriction
  on property: has_catalyst
  some values from: palladium atom
definition: A cross-coupling reaction where a thioester and an organozinc halide react to form a ketone. It uses a palladium catalyst.
database_cross_reference: https://www.wikidata.org/wiki/Q5507762
has_obo_namespace: RXNO
id: RXNO:0000605

Axiom
annotated source: Fukuyama coupling
annotated property: definition
annotated target: A cross-coupling reaction where a thioester and an organozinc halide react to form a ketone. It uses a palladium catalyst.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

chloride Finkelstein reaction
type: Class
subclass of: Finkelstein reaction
definition: The conversion of an alkyl chloride to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation.
has_obo_namespace: RXNO
id: RXNO:0000606

Axiom
annotated source: chloride Finkelstein reaction
annotated property: definition
annotated target: The conversion of an alkyl chloride to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

bromide Finkelstein reaction
type: Class
subclass of: Finkelstein reaction
definition: The conversion of an alkyl bromide to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation.
has_obo_namespace: RXNO
id: RXNO:0000607

Axiom
annotated source: bromide Finkelstein reaction
annotated property: definition
annotated target: The conversion of an alkyl bromide to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

sulfonate ester Finkelstein reaction
type: Class
subclass of: Finkelstein reaction
definition: The conversion of an alkyl sulfonate ester to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation.
has_obo_namespace: RXNO
id: RXNO:0000608

Axiom
annotated source: sulfonate ester Finkelstein reaction
annotated property: definition
annotated target: The conversion of an alkyl sulfonate ester to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Sandmeyer fluorination
type: Class
subclass of: Sandmeyer halogenation
definition: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) fluoride to form an aromatic fluoride.
has_obo_namespace: RXNO
id: RXNO:0000609

Axiom
annotated source: Sandmeyer fluorination
annotated property: definition
annotated target: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) fluoride to form an aromatic fluoride.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Sandmeyer chlorination
type: Class
subclass of: Sandmeyer halogenation
definition: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) chloride to form an aromatic chloride.
has_obo_namespace: RXNO
id: RXNO:0000610

Axiom
annotated source: Sandmeyer chlorination
annotated property: definition
annotated target: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) chloride to form an aromatic chloride.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Sandmeyer bromination
type: Class
subclass of: Sandmeyer halogenation
definition: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) bromide to form an aromatic bromide.
has_obo_namespace: RXNO
id: RXNO:0000611

Axiom
annotated source: Sandmeyer bromination
annotated property: definition
annotated target: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) bromide to form an aromatic bromide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Sandmeyer iodination
type: Class
subclass of: Sandmeyer halogenation
definition: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) iodide to form an aromatic iodide.
has_obo_namespace: RXNO
id: RXNO:0000612

Axiom
annotated source: Sandmeyer iodination
annotated property: definition
annotated target: An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) iodide to form an aromatic iodide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

imidazole synthesis
type: Class
subclass of: azacycle synthesis
definition: A planned reaction in which one of the products contains an imidazole system that was not in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000613

Axiom
annotated source: imidazole synthesis
annotated property: definition
annotated target: A planned reaction in which one of the products contains an imidazole system that was not in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

indazole synthesis
type: Class
subclass of: azacycle synthesis
definition: A planned reaction in which one of the products contains an indazole system that was not in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000614

Axiom
annotated source: indazole synthesis
annotated property: definition
annotated target: A planned reaction in which one of the products contains an indazole system that was not in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

piperazine synthesis
type: Class
subclass of: azacycle synthesis
definition: A planned reaction in which one of the products contains a piperazine system that was not in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000615

Axiom
annotated source: piperazine synthesis
annotated property: definition
annotated target: A planned reaction in which one of the products contains a piperazine system that was not in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

piperidine synthesis
type: Class
subclass of: azacycle synthesis
definition: A planned reaction in which one of the products contains a piperidine system that was not in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000616

Axiom
annotated source: piperidine synthesis
annotated property: definition
annotated target: A planned reaction in which one of the products contains a piperidine system that was not in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

pyrrolidine synthesis
type: Class
subclass of: azacycle synthesis
definition: A planned reaction in which one of the products contains a pyrrolidine system that was not in any of the reactants.
has_obo_namespace: RXNO
id: RXNO:0000617

Axiom
annotated source: pyrrolidine synthesis
annotated property: definition
annotated target: A planned reaction in which one of the products contains a pyrrolidine system that was not in any of the reactants.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Hofmann-Löffler-Freytag reaction
type: Class
equivalent class: Class
  union of: Hofmann-Löffler-Freytag piperidine synthesis
  union of: Hofmann-Löffler-Freytag pyrrolidine synthesis
subclass of: azacycle synthesis
definition: An azacycle synthesis in which pyrrolidines or piperidines are formed by decomposition of protonated N-haloamines.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r207/
database_cross_reference: https://www.wikidata.org/wiki/Q5876831
has_exact_synonym: Hofmann-Löffler reaction
has_obo_namespace: RXNO
id: RXNO:0000618

Axiom
annotated source: Hofmann-Löffler-Freytag reaction
annotated property: definition
annotated target: An azacycle synthesis in which pyrrolidines or piperidines are formed by decomposition of protonated N-haloamines.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r207/hofmann-löffler-freytag%20reaction

Hofmann-Löffler-Freytag piperidine synthesis
type: Class
subclass of: piperidine synthesis
definition: A Hofmann-Löffler-Freytag reaction in which the product is a piperidine.
has_obo_namespace: RXNO
id: RXNO:0000619

Axiom
annotated source: Hofmann-Löffler-Freytag piperidine synthesis
annotated property: definition
annotated target: A Hofmann-Löffler-Freytag reaction in which the product is a piperidine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Hofmann-Löffler-Freytag pyrrolidine synthesis
type: Class
subclass of: pyrrolidine synthesis
definition: A Hofmann-Löffler-Freytag reaction in which the product is a pyrrolidine.
has_obo_namespace: RXNO
id: RXNO:0000620

Axiom
annotated source: Hofmann-Löffler-Freytag pyrrolidine synthesis
annotated property: definition
annotated target: A Hofmann-Löffler-Freytag reaction in which the product is a pyrrolidine.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Hell-Volhard-Zelinsky reaction
type: Class
subclass of: halogenation
subclass of: Restriction
  on property: has specified reactant
  some values from: dibromine
subclass of: Restriction
  on property: has specified reactant
  some values from: carboxylic acid
subclass of: Restriction
  on property: has_catalyst
  some values from: phosphorus atom
definition: An alpha-halogenation reaction where a carboxylic acid reacts with dibromine to form an alpha-bromocarboxylic acid.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r194
database_cross_reference: https://www.wikidata.org/wiki/Q902219
has_exact_synonym: Hell-Volhard-Zelinsky halogenation
has_obo_namespace: RXNO
id: RXNO:0000621

Axiom
annotated source: Hell-Volhard-Zelinsky reaction
annotated property: definition
annotated target: An alpha-halogenation reaction where a carboxylic acid reacts with dibromine to form an alpha-bromocarboxylic acid.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Meerwein-Ponndorf-Verley reduction of an aldehyde
type: Class
subclass of: functional group reduction
subclass of: Meerwein-Ponndorf-Verley reduction
subclass of: Restriction
  on property: has specified product
  some values from: primary alcohol
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
definition: Meerwein-Ponndorf-Verley reduction of an aldehyde to the corresponding primary alcohol.
has_obo_namespace: RXNO
id: RXNO:0000622

Axiom
annotated source: Meerwein-Ponndorf-Verley reduction of an aldehyde
annotated property: definition
annotated target: Meerwein-Ponndorf-Verley reduction of an aldehyde to the corresponding primary alcohol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Meerwein-Ponndorf-Verley reduction of a ketone
type: Class
subclass of: functional group reduction
subclass of: Meerwein-Ponndorf-Verley reduction
subclass of: Restriction
  on property: has specified product
  some values from: secondary alcohol
subclass of: Restriction
  on property: has specified reactant
  some values from: ketone
definition: Meerwein-Ponndorf-Verley reduction of a ketone to the corresponding secondary alcohol.
has_obo_namespace: RXNO
id: RXNO:0000623

Axiom
annotated source: Meerwein-Ponndorf-Verley reduction of a ketone
annotated property: definition
annotated target: Meerwein-Ponndorf-Verley reduction of a ketone to the corresponding secondary alcohol.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Heck-type reaction
type: Class
subclass of: carbon-carbon coupling reaction
definition: A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin.
has_obo_namespace: RXNO
id: RXNO:0000624

Axiom
annotated source: Heck-type reaction
annotated property: definition
annotated target: A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429

obsolete: bromo Heck reaction
type: Class
definition: A Heck reaction where an organobromide couples to a terminal olefin to produce an internal olefin, catalysed by palladium.
has_obo_namespace: RXNO
id: RXNO:0000625
deprecated: true

Axiom
annotated source: obsolete: bromo Heck reaction
annotated property: definition
annotated target: A Heck reaction where an organobromide couples to a terminal olefin to produce an internal olefin, catalysed by palladium.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429

chloro Heck reaction
type: Class
subclass of: Heck reaction
subclass of: chloro Heck-type reaction
definition: A Heck reaction where an organochloride couples to a terminal olefin to produce an internal olefin, catalysed by palladium.
has_obo_namespace: RXNO
id: RXNO:0000626

Axiom
annotated source: chloro Heck reaction
annotated property: definition
annotated target: A Heck reaction where an organochloride couples to a terminal olefin to produce an internal olefin, catalysed by palladium.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429

iodo Heck reaction
type: Class
subclass of: Heck reaction
definition: A Heck reaction where an organoiodide couples to a terminal olefin to produce an internal olefin, catalysed by palladium.
has_obo_namespace: RXNO
id: RXNO:0000627

Axiom
annotated source: iodo Heck reaction
annotated property: definition
annotated target: A Heck reaction where an organoiodide couples to a terminal olefin to produce an internal olefin, catalysed by palladium.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429

triflyloxy Heck reaction
type: Class
subclass of: Heck reaction
definition: A Heck reaction where an organotriflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium.
has_obo_namespace: RXNO
id: RXNO:0000628

Axiom
annotated source: triflyloxy Heck reaction
annotated property: definition
annotated target: A Heck reaction where an organotriflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429

bromo Heck-type reaction
type: Class
subclass of: Heck-type reaction
definition: A Heck-type reaction where an organobromide couples to a terminal olefin to produce an internal olefin.
has_obo_namespace: RXNO
id: RXNO:0000629

Axiom
annotated source: bromo Heck-type reaction
annotated property: definition
annotated target: A Heck-type reaction where an organobromide couples to a terminal olefin to produce an internal olefin.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429

chloro Heck-type reaction
type: Class
subclass of: Heck-type reaction
definition: A Heck-type reaction where an organochloride couples to a terminal olefin to produce an internal olefin.
has_obo_namespace: RXNO
id: RXNO:0000630

Axiom
annotated source: chloro Heck-type reaction
annotated property: definition
annotated target: A Heck-type reaction where an organochloride couples to a terminal olefin to produce an internal olefin.
database_cross_reference: RSC:db
database_cross_reference: https://orcid.org/0000-0001-5985-7429

acyclic Beckmann rearrangement
type: Class
subclass of: Beckmann rearrangement
definition: A Beckmann rearrangement where an acyclic amide is formed.
database_cross_reference: NAMERXN:2.8.1
has_obo_namespace: RXNO
id: RXNO:0000631

Axiom
annotated source: acyclic Beckmann rearrangement
annotated property: definition
annotated target: A Beckmann rearrangement where an acyclic amide is formed.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Baeyer–Emmerling indole synthesis
type: Class
subclass of: indole synthesis
definition: An indole synthesis where an ortho-nitrocinnamic acid reacts with iron powder in a basic solution to form an indole.
database_cross_reference: NAMERXN:4.1.41
database_cross_reference: https://doi.org/10.1002/cber.186900201268
database_cross_reference: https://www.wikidata.org/wiki/Q3159940
has_obo_namespace: RXNO
id: RXNO:0000632

Axiom
annotated source: Baeyer–Emmerling indole synthesis
annotated property: definition
annotated target: An indole synthesis where an ortho-nitrocinnamic acid reacts with iron powder in a basic solution to form an indole.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

bromo Sonogashira coupling
type: Class
subclass of: Sonogashira coupling
definition: A Sonogashira coupling where the aryl halide is an aryl bromide.
database_cross_reference: NAMERXN:3.3.2
has_exact_synonym: Bromo Sonogashira coupling
has_obo_namespace: RXNO
id: RXNO:0000633

Axiom
annotated source: bromo Sonogashira coupling
annotated property: definition
annotated target: A Sonogashira coupling where the aryl halide is an aryl bromide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

bromo Suzuki coupling
type: Class
subclass of: Suzuki-Miyaura coupling
subclass of: bromo Suzuki-type coupling
definition: A Suzuki coupling where the halide is a bromide.
database_cross_reference: NAMERXN:3.1.1
has_exact_synonym: Bromo Suzuki coupling
has_exact_synonym: bromo Suzuki-Miyaura coupling
has_obo_namespace: RXNO
id: RXNO:0000634

Axiom
annotated source: bromo Suzuki coupling
annotated property: definition
annotated target: A Suzuki coupling where the halide is a bromide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

bromo Suzuki-type coupling
type: Class
subclass of: Suzuki-type coupling
definition: A Suzuki-type coupling where the halide is a bromide.
database_cross_reference: NAMERXN:3.1.5
has_exact_synonym: Bromo Suzuki-type coupling
has_exact_synonym: bromo Suzuki-Miyaura-type coupling
has_obo_namespace: RXNO
id: RXNO:0000635

Axiom
annotated source: bromo Suzuki-type coupling
annotated property: definition
annotated target: A Suzuki-type coupling where the halide is a bromide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

bromolactonization
type: Class
subclass of: halolactonization
definition: A halolactionization where the halide is a bromide.
database_cross_reference: NAMERXN:4.2.13
has_exact_synonym: bromolactonisation
has_obo_namespace: RXNO
id: RXNO:0000636

Axiom
annotated source: bromolactonization
annotated property: definition
annotated target: A halolactionization where the halide is a bromide.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

chloro Sonogashira coupling
type: Class
subclass of: Sonogashira coupling
definition: A Sonogashira coupling where the aryl halide is an aryl chloride.
database_cross_reference: NAMERXN:3.3.3
has_exact_synonym: Chloro Sonogashira coupling
has_obo_namespace: RXNO
id: RXNO:0000637

Axiom
annotated source: chloro Sonogashira coupling
annotated property: definition
annotated target: A Sonogashira coupling where the aryl halide is an aryl chloride.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

chloro Suzuki coupling
type: Class
subclass of: Suzuki-Miyaura coupling
subclass of: chloro Suzuki-type coupling
definition: A Suzuki coupling where the halide is a chloride.
database_cross_reference: NAMERXN:3.1.2
has_exact_synonym: Chloro Suzuki coupling
has_exact_synonym: chloro Suzuki-Miyaura coupling
has_obo_namespace: RXNO
id: RXNO:0000638

Axiom
annotated source: chloro Suzuki coupling
annotated property: definition
annotated target: A Suzuki coupling where the halide is a chloride.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

chloro Suzuki-type coupling
type: Class
subclass of: Suzuki-type coupling
definition: A Suzuki-type coupling where the halide is a chloride.
database_cross_reference: NAMERXN:3.1.6
has_exact_synonym: Chloro Suzuki-type coupling
has_exact_synonym: chloro Suzuki-Miyaura-type coupling
has_obo_namespace: RXNO
id: RXNO:0000639

Axiom
annotated source: chloro Suzuki-type coupling
annotated property: definition
annotated target: A Suzuki-type coupling where the halide is a chloride.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

chlorolactonization
type: Class
subclass of: halolactonization
definition: A halolactionization where the halide is a chloride.
database_cross_reference: NAMERXN:4.2.14
has_exact_synonym: chlorolactonisation
has_obo_namespace: RXNO
id: RXNO:0000640

Axiom
annotated source: chlorolactonization
annotated property: definition
annotated target: A halolactionization where the halide is a chloride.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Conrad-Limpach cyclisation
type: Class
subclass of: dealcoholative condensation
definition: Reaction of an arylamine wtih a beta-ketoester to yield a 4-hydroxyquinoline.
database_cross_reference: https://en.wikipedia.org/wiki/Conrad%E2%80%93Limpach_synthesis
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r84/
database_cross_reference: https://www.wikidata.org/wiki/Q1944895
has_exact_synonym: Conrad-Limpach cyclization
has_exact_synonym: Conrad-Limpach synthesis
has_obo_namespace: RXNO
id: RXNO:0000641

Axiom
annotated source: Conrad-Limpach cyclisation
annotated property: definition
annotated target: Reaction of an arylamine wtih a beta-ketoester to yield a 4-hydroxyquinoline.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Combes quinoline synthesis
type: Class
subclass of: molecular dehydration reaction
subclass of: quinoline synthesis
definition: Reaction of a beta-diketone with a primary arylamine to yield a quinoline. It is acid-catalysed.
database_cross_reference: https://en.wikipedia.org/wiki/Combes_quinoline_synthesis
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r83/
database_cross_reference: https://www.wikidata.org/wiki/Q1058068
has_obo_namespace: RXNO
id: RXNO:0000642

Axiom
annotated source: Combes quinoline synthesis
annotated property: definition
annotated target: Reaction of a beta-diketone with a primary arylamine to yield a quinoline. It is acid-catalysed.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Prato reaction
type: Class
subclass of: 1,3-dipolar cycloaddition
definition: A 1,3-dipolar cycloaddition reaction where a fullerene reacts with an aldehyde and an amino acid to form a pyrrolidinofullerene.
database_cross_reference: https://www.wikidata.org/wiki/Q4391481
has_obo_namespace: RXNO
id: RXNO:0000643

Axiom
annotated source: Prato reaction
annotated property: definition
annotated target: A 1,3-dipolar cycloaddition reaction where a fullerene reacts with an aldehyde and an amino acid to form a pyrrolidinofullerene.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Piancatelli rearrangement
type: Class
subclass of: rearrangement step
definition: A rearrangement of a 2-furylcarbinol to a 4-hydroxycyclopentenone. It is acid-catalysed.
database_cross_reference: https://www.wikidata.org/wiki/Q3319193
has_obo_namespace: RXNO
id: RXNO:0000644

Axiom
annotated source: Piancatelli rearrangement
annotated property: definition
annotated target: A rearrangement of a 2-furylcarbinol to a 4-hydroxycyclopentenone. It is acid-catalysed.
database_cross_reference: https://orcid.org/0000-0001-5985-7429

retro-Prato reaction
type: Class
subclass of: ring breaking
definition: A ring-breaking reaction where a pyrrolidinofullerene yields a fullerene. The substituted fullerene is heated with a dipolarophile and a catalyst.
has_obo_namespace: RXNO
id: RXNO:0000645

Axiom
annotated source: retro-Prato reaction
annotated property: definition
annotated target: A ring-breaking reaction where a pyrrolidinofullerene yields a fullerene. The substituted fullerene is heated with a dipolarophile and a catalyst.
database_cross_reference: https://doi.org/10.1002/anie.200502556
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Bingel reaction
type: Class
subclass of: fused-ring-system formation
definition: A cycloaddition where a fullerene reacts with diethyl bromomalonate to form a methanofullerene.
database_cross_reference: https://www.wikidata.org/wiki/Q1054818
has_obo_namespace: RXNO
id: RXNO:0000646

Axiom
annotated source: Bingel reaction
annotated property: definition
annotated target: A cycloaddition where a fullerene reacts with diethyl bromomalonate to form a methanofullerene.
database_cross_reference: https://doi.org/10.1002/cber.19931260829
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Wacker cyclisation
type: Class
subclass of: 1,3-dipolar cycloaddition
definition: A cyclisation where a hydroxyl group acts as the nucleophile in a Wacker-Tsuji oxidation accompanied by beta-hydride elimination, forming a ring.
has_exact_synonym: Wacker cyclization
has_obo_namespace: RXNO
id: RXNO:0000647

Axiom
annotated source: Wacker cyclisation
annotated property: definition
annotated target: A cyclisation where a hydroxyl group acts as the nucleophile in a Wacker-Tsuji oxidation accompanied by beta-hydride elimination, forming a ring.
database_cross_reference: http://organicreactions.org/index.php/Wacker_oxidation
database_cross_reference: https://orcid.org/0000-0001-5985-7429

aza-Wacker cyclisation
type: Class
subclass of: 1,3-dipolar cycloaddition
definition: A cyclisation where an amino group acts as the nucleophile in a Wacker-Tsuji oxidation accompanied by beta-hydride elimination, forming a ring.
has_exact_synonym: aza-Wacker cyclization
has_obo_namespace: RXNO
id: RXNO:0000648

Axiom
annotated source: aza-Wacker cyclisation
annotated property: definition
annotated target: A cyclisation where an amino group acts as the nucleophile in a Wacker-Tsuji oxidation accompanied by beta-hydride elimination, forming a ring.
database_cross_reference: http://organicreactions.org/index.php/Wacker_oxidation
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Lemieux-Johnson oxidation
type: Class
subclass of: cleaving reaction
subclass of: alkene oxidative cleavage
subclass of: Restriction
  on property: has_part
  some values from: Malaprade reaction
definition: A cleaving reaction where an olefin is dihydroxylated with osmium tetroxide and undergoes a Malaprade reaction to yield two aldehydes, two ketones, or an aldehyde and a ketone.
database_cross_reference: https://www.wikidata.org/wiki/Q6521154
has_obo_namespace: RXNO
id: RXNO:0000649

Axiom
annotated source: Lemieux-Johnson oxidation
annotated property: definition
annotated target: A cleaving reaction where an olefin is dihydroxylated with osmium tetroxide and undergoes a Malaprade reaction to yield two aldehydes, two ketones, or an aldehyde and a ketone.
database_cross_reference: https://doi.org/10.1021/jo01110a606
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Malaprade reaction
type: Class
subclass of: cleaving reaction
subclass of: alkene oxidative cleavage
definition: A cleaving reaction of a 1,2-diol using periodic acid to give the corresponding carbonyl compounds.
database_cross_reference: https://www.wikidata.org/wiki/Q10851620
has_obo_namespace: RXNO
id: RXNO:0000650

Axiom
annotated source: Malaprade reaction
annotated property: definition
annotated target: A cleaving reaction of a 1,2-diol using periodic acid to give the corresponding carbonyl compounds.
database_cross_reference: https://doi.org/10.1039/C8CC09208G
database_cross_reference: https://orcid.org/0000-0001-5985-7429

Fenton 1,2-glycol oxidation
type: Class
subclass of: functional group oxidation
definition: The oxidation of a 1,2-glycol with Fenton's reagent (hydrogen peroxide and iron salts) to give an alpha-hydroxy aldehyde.
has_obo_namespace: RXNO
id: RXNO:0000651

Axiom
annotated source: Fenton 1,2-glycol oxidation
annotated property: definition
annotated target: The oxidation of a 1,2-glycol with Fenton's reagent (hydrogen peroxide and iron salts) to give an alpha-hydroxy aldehyde.
database_cross_reference: rsc:db

Fenton alpha-hydroxy carboxylic acid oxidation
type: Class
subclass of: functional group oxidation
definition: The oxidation of an alpha-hydroxy carboxylic acid with Fenton's reagent to give an alpha-keto carboxylic acid.
has_obo_namespace: RXNO
id: RXNO:0000652

Axiom
annotated source: Fenton alpha-hydroxy carboxylic acid oxidation
annotated property: definition
annotated target: The oxidation of an alpha-hydroxy carboxylic acid with Fenton's reagent to give an alpha-keto carboxylic acid.
database_cross_reference: RSC:db

Fenton hydrogen peroxide reduction
type: Class
subclass of: functional group oxidation
definition: The reaction of the components of Fenton's reagent, viz. reduction of hydrogen peroxide by Fe(II) , producing an hydroxyl radical.
has_obo_namespace: RXNO
id: RXNO:0000653

Axiom
annotated source: Fenton hydrogen peroxide reduction
annotated property: definition
annotated target: The reaction of the components of Fenton's reagent, viz. reduction of hydrogen peroxide by Fe(II) , producing an hydroxyl radical.
database_cross_reference: RSC:db

Mukaiyama hydration
type: Class
subclass of: addition reaction
subclass of: Restriction
  on property: has specified product
  some values from: alcohol
subclass of: Restriction
  on property: has specified reactant
  some values from: dioxygen
subclass of: Restriction
  on property: has specified reactant
  some values from: phenylsilane
subclass of: Restriction
  on property: has specified reactant
  some values from: alkene
definition: The Mukaiyama hydration is an organic reaction involving formal addition of an equivalent of water across an alkene by the action of catalytic bis(acetylacetonato)cobalt(II) complex, phenylsilane and atmospheric oxygen.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-05-11T07:40:36Z
has_obo_namespace: RXNO
id: RXNO:0000654

Axiom
annotated source: Mukaiyama hydration
annotated property: definition
annotated target: The Mukaiyama hydration is an organic reaction involving formal addition of an equivalent of water across an alkene by the action of catalytic bis(acetylacetonato)cobalt(II) complex, phenylsilane and atmospheric oxygen.
database_cross_reference: https://en.wikipedia.org/wiki/Mukaiyama_hydration

Favorskii reaction
type: Class
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has specified product
  some values from: alcohol
subclass of: Restriction
  on property: has specified reactant
  some values from: alkyne
subclass of: Restriction
  on property: has specified reactant
  some values from: carbonyl compound
definition: A reaction between an alkyne and a carbonyl group under basic conditions in which a terminal alkyne serves as the CH-acidic moiety. When the carbonyl is an aldehyde, the 'Favorskii rearrangement' (RXNO:0000385) takes place and leads to an enone.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-05-17T08:17:36Z
has_obo_namespace: RXNO
has_related_synonym: Faworski-Babayan reaction
id: RXNO:0000655

Axiom
annotated source: Favorskii reaction
annotated property: definition
annotated target: A reaction between an alkyne and a carbonyl group under basic conditions in which a terminal alkyne serves as the CH-acidic moiety. When the carbonyl is an aldehyde, the 'Favorskii rearrangement' (RXNO:0000385) takes place and leads to an enone.
database_cross_reference: https://en.wikipedia.org/wiki/Favorskii_reaction

Diimide reduction
type: Class
subclass of: addition reaction
subclass of: Restriction
  on property: has specified product
  some values from: dinitrogen
subclass of: Restriction
  on property: has specified product
  some values from: alkane
subclass of: Restriction
  on property: has specified reactant
  some values from: diazene
definition: Reductions with diimide are a chemical reactions that convert unsaturated organic compounds to reduced alkane products. In the process, diimide is oxidized to dinitrogen.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-05-17T08:35:08Z
has_obo_namespace: RXNO
id: RXNO:0000656

Axiom
annotated source: Diimide reduction
annotated property: definition
annotated target: Reductions with diimide are a chemical reactions that convert unsaturated organic compounds to reduced alkane products. In the process, diimide is oxidized to dinitrogen.
database_cross_reference: https://en.wikipedia.org/wiki/Reductions_with_diimide

carbonyl group protection
type: Class
subclass of: protection reaction
subclass of: Restriction
  on property: protects
  some values from: carbonyl group
subclass of: Restriction
  on property: has specified reactant
  some values from: carbonyl compound
definition: A protection reaction where the reactive centre is a carbonyl oxygen.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-05-17T09:33:23Z
has_obo_namespace: RXNO
id: RXNO:0000657

acetal protection
type: Class
subclass of: carbonyl group protection
subclass of: Restriction
  on property: protects
  some values from: carbonyl group
subclass of: Restriction
  on property: has specified product
  some values from: acetal
subclass of: Restriction
  on property: has specified reactant
  some values from: alcohol
subclass of: Restriction
  on property: has_intermediate
  some values from: hemiacetal
definition: The acid-catalyzed formation of an acetal (or ketal) to protect a carbonyl group by nucleophilic addition of an alcohol to an aldehyde (or ketone) with the elimination of water.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-05-17T09:38:59Z
has_obo_namespace: RXNO
has_related_synonym: acetalisation
has_related_synonym: acetalization
id: RXNO:0000658

Axiom
annotated source: acetal protection
annotated property: definition
annotated target: The acid-catalyzed formation of an acetal (or ketal) to protect a carbonyl group by nucleophilic addition of an alcohol to an aldehyde (or ketone) with the elimination of water.
database_cross_reference: https://en.wikipedia.org/wiki/Acetal

Miyaura borylation
type: Class
subclass of: molecular skeleton joining reaction
subclass of: Restriction
  on property: has specified product
  some values from: boronate
subclass of: Restriction
  on property: has_catalyst
  some values from: palladium atom
definition: A chemical reaction that allows the generation of boronates from vinyl or aryl halides with the cross-coupling of bis(pinacolato)diboron under basic conditions.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-11-04T10:48:44Z
has_exact_synonym: Miyaura boration
has_exact_synonym: Miyaura borylation reaction
has_obo_namespace: RXNO
id: RXNO:0000659

Axiom
annotated source: Miyaura borylation
annotated property: definition
annotated target: A chemical reaction that allows the generation of boronates from vinyl or aryl halides with the cross-coupling of bis(pinacolato)diboron under basic conditions.
database_cross_reference: https://www.organic-chemistry.org/namedreactions/miyaura-borylation-reaction.shtm
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r288/miyaura%20boration

Corey-Winter elimination
type: Class
subclass of: molecular skeleton elimination reaction
subclass of: Restriction
  on property: has specified product
  some values from: olefin
subclass of: Restriction
  on property: has specified reactant
  some values from: alcohol
definition: A chemical reaction for the stereoselective synthesis of an olefin from a 1,2-diol.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-11-04T11:03:16Z
has_obo_namespace: RXNO
has_related_synonym: Corey-Winter fragmentation
has_related_synonym: Corey-Winter olefination
has_related_synonym: Corey–Winter olefin synthesis
id: RXNO:0000660

Axiom
annotated source: Corey-Winter elimination
annotated property: definition
annotated target: A chemical reaction for the stereoselective synthesis of an olefin from a 1,2-diol.
database_cross_reference: https://en.wikipedia.org/wiki/Corey%E2%80%93Winter_olefin_synthesis
database_cross_reference: https://www.organic-chemistry.org/namedreactions/corey-winter-olefin-synthesis.shtm

Tsuji-Wilkinson decarbonylation
type: Class
subclass of: end-of-chain chain shortening
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: acyl chloride
definition: The Tsuji-Wilkinson decarbonylation reaction is a method for the decarbonylation of aldehydes and some acyl chlorides.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-11-04T12:09:26Z
has_obo_namespace: RXNO
id: RXNO:0000661

Axiom
annotated source: Tsuji-Wilkinson decarbonylation
annotated property: definition
annotated target: The Tsuji-Wilkinson decarbonylation reaction is a method for the decarbonylation of aldehydes and some acyl chlorides.
database_cross_reference: https://dbpedia.org/page/Tsuji%E2%80%93Wilkinson_decarbonylation_reaction
comment: Although decarbonylation can be effected by several transition metal complexes, Wilkinson's catalyst has proven the most effective.

Corey-Seebach reaction
type: Class
subclass of: functional group modification
subclass of: Restriction
  on property: has specified product
  some values from: ketone
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: propane-1,3-dithiol
subclass of: Restriction
  on property: has specified reactant
  some values from: butyllithium
definition: A chemical reaction in which ketones are synthesized from formaldehyde or other aldehydes, involving a temporary repolarization of a carbonyl group.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-11-05T07:51:22Z
has_obo_namespace: RXNO
has_related_synonym: Corey-Seebach Umpolung
has_related_synonym: Seebach Umpolung
id: RXNO:0000662

Axiom
annotated source: Corey-Seebach reaction
annotated property: definition
annotated target: A chemical reaction in which ketones are synthesized from formaldehyde or other aldehydes, involving a temporary repolarization of a carbonyl group.
database_cross_reference: https://en.wikipedia.org/wiki/Corey-Seebach_reaction
database_cross_reference: https://www.organic-chemistry.org/namedreactions/corey-seebach-reaction.shtm
comment: Usually, the aldehyde is first reacted with propane-1,3-dithiol to form a 1,3-dithiane, which then reacts with an electrophile after deprotonation with n-butyllithium.

nitroxide exchange reaction
type: Class
subclass of: functional group modification
subclass of: Restriction
  on property: has specified product
  some values from: aminoxyls
subclass of: Restriction
  on property: has specified reactant
  some values from: aminoxyls
definition: Nitroxide exchange reactions are based on thermal C–O bond homolysis of alkoxyamines, which leads to transient carbon-centred radicals and persistent nitroxide radicals. Usually these carbon centred radicals are quickly trapped by the nitroxide radicals and reform the alkoxyamines.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-11-12T08:28:13Z
has_obo_namespace: RXNO
id: RXNO:0000663
comment: IUPAC does not recommend the use of the often synonymously used terms "nitroxyl radicals" or "nitroxides" for the class of "aminoxyl radicals".

Axiom
annotated source: nitroxide exchange reaction
annotated property: definition
annotated target: Nitroxide exchange reactions are based on thermal C–O bond homolysis of alkoxyamines, which leads to transient carbon-centred radicals and persistent nitroxide radicals. Usually these carbon centred radicals are quickly trapped by the nitroxide radicals and reform the alkoxyamines.
database_cross_reference: C6RA06510D

Axiom
annotated source: nitroxide exchange reaction
annotated property: comment
annotated target: IUPAC does not recommend the use of the often synonymously used terms "nitroxyl radicals" or "nitroxides" for the class of "aminoxyl radicals".
database_cross_reference: goldbook.A00285
database_cross_reference: goldbook.N04171

Baeyer pyridine synthesis
type: Class
subclass of: functional group modification
subclass of: Restriction
  on property: has specified product
  some values from: pyridines
subclass of: Restriction
  on property: has specified reactant
  some values from: pyrans
definition: The conversion of pyran or pyrone (pyranone) derivatives to the corresponding pyridine derivative.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-11-12T09:25:38Z
has_obo_namespace: RXNO
id: RXNO:0000664

Axiom
annotated source: Baeyer pyridine synthesis
annotated property: definition
annotated target: The conversion of pyran or pyrone (pyranone) derivatives to the corresponding pyridine derivative.
database_cross_reference: cr60130a004

Corey-Kim oxidation
type: Class
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified product
  some values from: ketone
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: primary alcohol
subclass of: Restriction
  on property: has specified reactant
  some values from: secondary alcohol
definition: Oxidation of primary and secondary alcohols via their alkoxysulfonium salts. Upon the addition of base, the salt rearranges intramolecularly to aldehydes and ketones, respectively.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-11-15T08:58:15Z
has_obo_namespace: RXNO
has_related_synonym: Corey-Kim reaction
id: RXNO:0000665

Axiom
annotated source: Corey-Kim oxidation
annotated property: definition
annotated target: Oxidation of primary and secondary alcohols via their alkoxysulfonium salts. Upon the addition of base, the salt rearranges intramolecularly to aldehydes and ketones, respectively.
database_cross_reference: corey-kim oxidation

Corey-Suggs oxidation
type: Class
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified product
  some values from: ketone
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: primary alcohol
subclass of: Restriction
  on property: has specified reactant
  some values from: secondary alcohol
definition: Oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, through the use of pyridinium chlorochromate (PCC).
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-11-15T09:09:31Z
has_obo_namespace: RXNO
has_related_synonym: PCC oxidation
id: RXNO:0000666

Axiom
annotated source: Corey-Suggs oxidation
annotated property: definition
annotated target: Oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, through the use of pyridinium chlorochromate (PCC).
database_cross_reference: corey-suggs pcc oxidation

Corey-Schmidt oxidation
type: Class
subclass of: functional group oxidation
definition: Oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, through the use of pyridinium dichromate (PDC).
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-11-15T09:20:03Z
has_obo_namespace: RXNO
has_related_synonym: PDC oxidation
id: RXNO:0000667

Axiom
annotated source: Corey-Schmidt oxidation
annotated property: definition
annotated target: Oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, through the use of pyridinium dichromate (PDC).
database_cross_reference: corey-schmidt-oxidation

Albright-Goldman oxidation
type: Class
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified product
  some values from: ketone
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: primary alcohol
subclass of: Restriction
  on property: has specified reactant
  some values from: secondary alcohol
definition: A particularly mild oxidation method in which, for example, dimethyl sulfoxide and acetic anhydride can be used as oxidizing agents to selectively produce aldehydes from primary alcohols without further oxidation to carboxylic acids. Analogously, secondary alcohols can be oxidized to form ketones.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-11-15T09:30:47Z
has_obo_namespace: RXNO
id: RXNO:0000668

Axiom
annotated source: Albright-Goldman oxidation
annotated property: definition
annotated target: A particularly mild oxidation method in which, for example, dimethyl sulfoxide and acetic anhydride can be used as oxidizing agents to selectively produce aldehydes from primary alcohols without further oxidation to carboxylic acids. Analogously, secondary alcohols can be oxidized to form ketones.
database_cross_reference: Albright-Goldman oxidation

Rubottom oxidation
type: Class
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified product
  some values from: alpha-hydroxy ketone
subclass of: Restriction
  on property: has specified product
  some values from: silyl enol ether
subclass of: Restriction
  on property: has specified product
  some values from: hydroxyaldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: peroxy acid
definition: The Rubottom oxidation is a useful, high-yielding chemical reaction between silyl enol ethers and peroxy acids to give the corresponding α-hydroxy carbonyl product.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-11-15T09:44:42Z
has_obo_namespace: RXNO
has_related_synonym: Rubottom reaction
id: RXNO:0000669

Axiom
annotated source: Rubottom oxidation
annotated property: definition
annotated target: The Rubottom oxidation is a useful, high-yielding chemical reaction between silyl enol ethers and peroxy acids to give the corresponding α-hydroxy carbonyl product.
database_cross_reference: Rubottom oxidation

Groebke-Blackburn-Bienaymé reaction
type: Class
subclass of: fused-ring-system formation
subclass of: Restriction
  on property: has specified product
  some values from: organic heteropolycyclic compound
subclass of: Restriction
  on property: has specified reactant
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: amidine
subclass of: Restriction
  on property: has specified reactant
  some values from: isocyanide
definition: A three-component reaction (3CR) of a heterocyclic amidine, an aldehyde, and an isocyanide, resulting in a cyclic compound with imidazo[1,2-a] heterocycle as the core structure.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-03T09:13:40Z
has_exact_synonym: GBB reaction
has_exact_synonym: GBB‐3CR reaction
has_obo_namespace: RXNO
id: RXNO:0000670

Axiom
annotated source: Groebke-Blackburn-Bienaymé reaction
annotated property: definition
annotated target: A three-component reaction (3CR) of a heterocyclic amidine, an aldehyde, and an isocyanide, resulting in a cyclic compound with imidazo[1,2-a] heterocycle as the core structure.
database_cross_reference: https://doi.org/10.1002/ejoc.201901124

Baeyer oxindole synthesis
type: Class
subclass of: fused-ring-system formation
subclass of: Restriction
  on property: has specified product
  some values from: indolin-2-one
definition: The preparation of oxindole/indolin-2-one from 2-nitrophenylacetic acid by reduction of the nitro group and subsequent dehydration.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-03T14:20:07Z
has_obo_namespace: RXNO
has_related_synonym: Baeyer indolinone synthesis
id: RXNO:0000671

Axiom
annotated source: Baeyer oxindole synthesis
annotated property: definition
annotated target: The preparation of oxindole/indolin-2-one from 2-nitrophenylacetic acid by reduction of the nitro group and subsequent dehydration.
database_cross_reference: https://doi.org/10.1021/cr60118a003

Leimgruber-Batcho indole synthesis
type: Class
subclass of: indole synthesis
subclass of: Restriction
  on property: has specified product
  some values from: indoles
subclass of: Restriction
  on property: has specified reactant
  some values from: nitrotoluene
definition: Condensation of a formamide acetal with a derivative of o-nitrotoluene to yield an enamine intermediate that subsequently undergoes reductive cyclization to give the corresponding indole.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-03T14:45:01Z
has_exact_synonym: Batcho-Leimgruber indole synthesis
has_obo_namespace: RXNO
id: RXNO:0000672

Axiom
annotated source: Leimgruber-Batcho indole synthesis
annotated property: definition
annotated target: Condensation of a formamide acetal with a derivative of o-nitrotoluene to yield an enamine intermediate that subsequently undergoes reductive cyclization to give the corresponding indole.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r253/leimgruber-batcho%20indole%20synthesis

IBX oxidation
type: Class
subclass of: functional group oxidation
subclass of: Restriction
  on property: has specified product
  some values from: ketone
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
subclass of: Restriction
  on property: has specified reactant
  some values from: primary alcohol
subclass of: Restriction
  on property: has specified reactant
  some values from: secondary alcohol
definition: Oxidation of alcohols to the corresponding carbonyl product using 2-iodoxybenzoic acid (IBX) as oxidizing agent.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-11-15T11:24:35Z
has_obo_namespace: RXNO
id: RXNO:0000673
comment: IBX oxidation and Dess-Martin oxidation are alcohol oxidation by hypervalent iodine reagents. The Dess-Martin periodinane used for oxidation in the Dess-Martin oxidation is prepared by reacting IBX with acetic anhydride in DMSO.

Axiom
annotated source: IBX oxidation
annotated property: definition
annotated target: Oxidation of alcohols to the corresponding carbonyl product using 2-iodoxybenzoic acid (IBX) as oxidizing agent.
database_cross_reference: ol026427n

decarboxylative cross-coupling
type: Class
subclass of: cross-coupling
subclass of: Restriction
  on property: has specified product
  some values from: carbon dioxide
subclass of: Restriction
  on property: has specified reactant
  some values from: organohalogen compound
subclass of: Restriction
  on property: has specified reactant
  some values from: carboxylic acid
definition: A chemical reaction in which a carboxylic acid (or its salt) reacts with an organic (alkyl or aryl) halide to form a new carbon-carbon bond with concomitant loss of CO2. In addition, the reaction requires a metal catalyst, a base and an oxidizing agent.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-06T08:44:51Z
has_obo_namespace: RXNO
id: RXNO:0000674

Axiom
annotated source: decarboxylative cross-coupling
annotated property: definition
annotated target: A chemical reaction in which a carboxylic acid (or its salt) reacts with an organic (alkyl or aryl) halide to form a new carbon-carbon bond with concomitant loss of CO2. In addition, the reaction requires a metal catalyst, a base and an oxidizing agent.
database_cross_reference: https://en.wikipedia.org/wiki/Decarboxylative_cross-coupling

Balsohn alkylation
type: Class
subclass of: carbon-carbon coupling reaction
subclass of: Restriction
  on property: has specified reactant
  some values from: alkene
subclass of: Restriction
  on property: has specified reactant
  some values from: arene
definition: A carbon-carbon coupling reaction between an arene and an alkene to give a substituted arene. The reaction is catalysed by a Lewis acid.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-06T11:08:37Z
has_obo_namespace: RXNO
id: RXNO:0000675

Axiom
annotated source: Balsohn alkylation
annotated property: definition
annotated target: A carbon-carbon coupling reaction between an arene and an alkene to give a substituted arene. The reaction is catalysed by a Lewis acid.
database_cross_reference: https://second.wiki/wiki/balsohn-alkylierung

Kabachnik-Fields reaction
type: Class
subclass of: molecular dehydration reaction
subclass of: molecular skeleton joining reaction
subclass of: Class
  intersection of: Class
    union of: aldehyde
    union of: Restriction
      on property: has specified reactant
      some values from: ketone
  intersection of: Class
    union of: secondary amine
    union of: Restriction
      on property: has specified reactant
      some values from: primary amine
  intersection of: Restriction
    on property: has specified reactant
    some values from: alkylphosphonate
subclass of: Restriction
  on property: has specified product
  some values from: aminophosphonate
definition: A three-component condensation reaction in which primary or secondary amines react with a carbonyl compound (aldehyde or ketone) and a dialkyl phosphonate (also called dialkyl phosphite) to form an alpha-aminophosphonate.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-13T11:39:08Z
has_obo_namespace: RXNO
has_related_synonym: phospha-Mannich reaction
id: RXNO:0000676

Axiom
annotated source: Kabachnik-Fields reaction
annotated property: definition
annotated target: A three-component condensation reaction in which primary or secondary amines react with a carbonyl compound (aldehyde or ketone) and a dialkyl phosphonate (also called dialkyl phosphite) to form an alpha-aminophosphonate.
database_cross_reference: https://doi.org/10.3390/molecules171112821

Baekeland-Manasse-Lederer reaction
type: Class
subclass of: polymerisation reaction
subclass of: Class
  intersection of: Restriction
    on property: has specified reactant
    some values from: phenol
  intersection of: Restriction
    on property: has specified reactant
    some values from: formaldehyde
definition: A polymerisation reaction in which phenol and formaldehyde react together in a chain reaction to form a phenol formaldehyde resin (also infrequently called phenoplast).
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-13T12:52:17Z
has_obo_namespace: RXNO
id: RXNO:0000677

Axiom
annotated source: Baekeland-Manasse-Lederer reaction
annotated property: definition
annotated target: A polymerisation reaction in which phenol and formaldehyde react together in a chain reaction to form a phenol formaldehyde resin (also infrequently called phenoplast).
database_cross_reference: https://doi.org/10.1021/ie50003a004

Aston-Greenburg rearrangement
type: Class
subclass of: rearrangement step
subclass of: Restriction
  on property: has specified product
  some values from: carboxylic ester
subclass of: Restriction
  on property: has specified reactant
  some values from: alpha-haloketone
definition: The rearrangement of an alpha-haloketone into an ester with a tertiary alpha-carbon atom by intramolecular migration of an alkyl or aryl group.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-14T08:15:45Z
has_obo_namespace: RXNO
id: RXNO:0000678

Axiom
annotated source: Aston-Greenburg rearrangement
annotated property: definition
annotated target: The rearrangement of an alpha-haloketone into an ester with a tertiary alpha-carbon atom by intramolecular migration of an alkyl or aryl group.
database_cross_reference: https://doi.org/10.1021/ja01867a003

Baddeley isomerization
type: Class
subclass of: rearrangement step
subclass of: Class
  union of: Restriction
    on property: has specified product
    some values from: polycyclic arene
  union of: Restriction
    on property: has specified product
    some values from: alkylbenzene
subclass of: Class
  union of: Restriction
    on property: has specified reactant
    some values from: polycyclic arene
  union of: Restriction
    on property: has specified reactant
    some values from: alkylbenzene
definition: The rearrangement/migration of alkyl groups in polyalkylbenzenes or polynuclear aromatic compounds in the presence of anhydrous aluminum chloride or the mixture of protonic acid and Lewis acid.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-14T08:45:33Z
has_obo_namespace: RXNO
id: RXNO:0000679

Axiom
annotated source: Baddeley isomerization
annotated property: definition
annotated target: The rearrangement/migration of alkyl groups in polyalkylbenzenes or polynuclear aromatic compounds in the presence of anhydrous aluminum chloride or the mixture of protonic acid and Lewis acid.
database_cross_reference: https://doi.org/10.1002/9780470638859.conrr030

Fukuyama reduction
type: Class
subclass of: functional group reduction
subclass of: Class
  intersection of: Restriction
    on property: has specified reactant
    some values from: organosilicon compound
  intersection of: Restriction
    on property: has specified reactant
    some values from: thioester
subclass of: Restriction
  on property: has specified product
  some values from: aldehyde
subclass of: Restriction
  on property: has_catalyst
  some values from: palladium atom
definition: The reduction of a thioester to an aldehyde by a silyl hydride in the presence of catalytic amounts of palladium.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-14T09:43:52Z
has_obo_namespace: RXNO
id: RXNO:0000680

Axiom
annotated source: Fukuyama reduction
annotated property: definition
annotated target: The reduction of a thioester to an aldehyde by a silyl hydride in the presence of catalytic amounts of palladium.
database_cross_reference: https://en.wikipedia.org/wiki/Fukuyama_reduction
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r163/fukuyama%20reduction

Dötz reaction
type: Class
subclass of: ring formation reaction step
subclass of: Class
  intersection of: Restriction
    on property: has specified reactant
    some values from: carbon monoxide
  intersection of: Restriction
    on property: has specified reactant
    some values from: alkyne
subclass of: Restriction
  on property: has specified product
  some values from: phenols
definition: A three component cyclization of an aromatic or vinylic alkoxy pentacarbonyl chromium carbene complex, an alkyne and carbon monoxide to give a Cr(CO)3 coordinated phenol.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-14T10:45:04Z
has_obo_namespace: RXNO
has_related_synonym: Doetz reaction
has_related_synonym: Wulff-Dötz reaction
has_related_synonym: benzannulation reaction of Fischer carbene complexes
id: RXNO:0000681

Axiom
annotated source: Dötz reaction
annotated property: definition
annotated target: A three component cyclization of an aromatic or vinylic alkoxy pentacarbonyl chromium carbene complex, an alkyne and carbon monoxide to give a Cr(CO)3 coordinated phenol.
database_cross_reference: https://en.wikipedia.org/wiki/Wulff%E2%80%93D%C3%B6tz_reaction
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r116/d%C3%B6tz%20reaction

Kulinkovich reaction
type: Class
subclass of: ring formation reaction step
subclass of: Class
  intersection of: Restriction
    on property: has specified reactant
    some values from: carboxylic ester
  intersection of: Restriction
    on property: has specified reactant
    some values from: organomagnesium halide
subclass of: Restriction
  on property: has specified product
  some values from: cyclopropanes
subclass of: Restriction
  on property: has specified reactant
  some values from: alkene
subclass of: Restriction
  on property: has_catalyst
  some values from: titanium atom
definition: The formation of a substituted cyclopropanol by reaction of a carboxylic ester with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. A modified cyclopropanol product can be generated by addition of a terminal alkene as a further reactant.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-15T09:10:05Z
has_obo_namespace: RXNO
id: RXNO:0000682
comment: The dialkyldialkoxytitanium reagent, which actually reacts with the carboxylic ester, is generated in situ from the Grignard reagent and the titanium(IV) alkoxide.

Axiom
annotated source: Kulinkovich reaction
annotated property: definition
annotated target: The formation of a substituted cyclopropanol by reaction of a carboxylic ester with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. A modified cyclopropanol product can be generated by addition of a terminal alkene as a further reactant.
database_cross_reference: https://en.wikipedia.org/wiki/Kulinkovich_reaction
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r247/kulinkovich%20reaction

Kulinkovich-de Meijere reaction
type: Class
subclass of: ring formation reaction step
subclass of: Class
  intersection of: Restriction
    on property: has specified reactant
    some values from: carboxamide
  intersection of: Restriction
    on property: has specified reactant
    some values from: organomagnesium halide
subclass of: Restriction
  on property: has specified product
  some values from: cyclopropanes
subclass of: Restriction
  on property: has_catalyst
  some values from: titanium atom
definition: The formation of a substituted cyclopropylamine by reaction of an amide with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-15T10:14:52Z
has_obo_namespace: RXNO
id: RXNO:0000683
comment: The Kulinkovich-de Meijere reaction is a modification of the Kulinkovich reaction (i.e., the reaction of an amide instead of a carboxylic ester under Kulinkovich conditions).

Axiom
annotated source: Kulinkovich-de Meijere reaction
annotated property: definition
annotated target: The formation of a substituted cyclopropylamine by reaction of an amide with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst.
database_cross_reference: https://en.wikipedia.org/wiki/Kulinkovich_reaction
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r247/kulinkovich%20reaction

Kulinkovich-Szymoniak reaction
type: Class
subclass of: ring formation reaction step
subclass of: Class
  intersection of: Restriction
    on property: has specified reactant
    some values from: nitrile
  intersection of: Restriction
    on property: has specified reactant
    some values from: organomagnesium halide
subclass of: Restriction
  on property: has specified product
  some values from: cyclopropanes
subclass of: Restriction
  on property: has_catalyst
  some values from: titanium atom
definition: The formation of a substituted primary cyclopropylamine by reaction of a nitrile with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-15T10:47:43Z
has_obo_namespace: RXNO
id: RXNO:0000684
comment: The Kulinkovich-Szymoniak reaction is a modification of the Kulinkovich reaction (i.e., the reaction of a nitrile instead of a carboxylic ester under Kulinkovich conditions).

Axiom
annotated source: Kulinkovich-Szymoniak reaction
annotated property: definition
annotated target: The formation of a substituted primary cyclopropylamine by reaction of a nitrile with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst.
database_cross_reference: https://en.wikipedia.org/wiki/Kulinkovich_reaction
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r247/kulinkovich%20reaction

Jacobsen epoxidation
type: Class
subclass of: epoxidation
subclass of: ring formation reaction step
subclass of: Restriction
  on property: has specified product
  some values from: epoxide
subclass of: Restriction
  on property: has specified reactant
  some values from: alkene
subclass of: Restriction
  on property: has_catalyst
  some values from: manganese atom
definition: Chiral (salen)manganese(III)-catalyzed asymmetric epoxidation of alkenes. In addition to the catalyst, stoichiometric amounts of an oxidant (e.g. sodium hypochlorite) are required.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-16T08:34:02Z
has_obo_namespace: RXNO
has_related_synonym: Jacobsen-Katsuki epoxidation
id: RXNO:0000686

Axiom
annotated source: Jacobsen epoxidation
annotated property: definition
annotated target: Chiral (salen)manganese(III)-catalyzed asymmetric epoxidation of alkenes. In addition to the catalyst, stoichiometric amounts of an oxidant (e.g. sodium hypochlorite) are required.
database_cross_reference: https://en.wikipedia.org/wiki/Jacobsen_epoxidation
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r218/jacobsen%20epoxidation

Shi epoxidation
type: Class
subclass of: epoxidation
subclass of: ring formation reaction step
subclass of: Restriction
  on property: has specified product
  some values from: epoxide
subclass of: Restriction
  on property: has specified reactant
  some values from: alkene
definition: Organocatalytic enantioselective epoxidation of trans- and tri-substituted olefins using a fructose derived chiral ketone catalyst and potassium peroxomonosulfate or H2O2 as an oxidant.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-16T08:57:48Z
has_obo_namespace: RXNO
id: RXNO:0000687

Axiom
annotated source: Shi epoxidation
annotated property: definition
annotated target: Organocatalytic enantioselective epoxidation of trans- and tri-substituted olefins using a fructose derived chiral ketone catalyst and potassium peroxomonosulfate or H2O2 as an oxidant.
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r399/shi%20epoxidation

Asinger reaction
type: Class
subclass of: ring formation reaction step
subclass of: thiacycle synthesis
subclass of: Class
  intersection of: Class
    union of: aldehyde
    union of: Restriction
      on property: has specified reactant
      some values from: ketone
  intersection of: Restriction
    on property: has specified reactant
    some values from: ammonia
  intersection of: Restriction
    on property: has specified reactant
    some values from: elemental sulfur
  intersection of: Restriction
    on property: has specified reactant
    some values from: carbonyl compound
subclass of: Restriction
  on property: has specified product
  some values from: thiazoles
definition: A multicomponent reaction (A-4CR) in which 3-thiazolines (2,5-dihydro-1,3-thiazoles) or mixtures of several 3-thiazolines are synthesized from elemental sulfur, an alpha-substitutable ketone or aldehyde, another carbonyl component and ammonia.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-16T09:29:30Z
has_obo_namespace: RXNO
has_related_synonym: Asinger thiazoline synthesis
has_related_synonym: Asinger-4 component reaction (A-4CR)
id: RXNO:0000688

Axiom
annotated source: Asinger reaction
annotated property: definition
annotated target: A multicomponent reaction (A-4CR) in which 3-thiazolines (2,5-dihydro-1,3-thiazoles) or mixtures of several 3-thiazolines are synthesized from elemental sulfur, an alpha-substitutable ketone or aldehyde, another carbonyl component and ammonia.
database_cross_reference: https://doi.org/10.1002/cmdc.202100086
database_cross_reference: https://en.wikipedia.org/wiki/Asinger_reaction

haloform reaction
type: Class
subclass of: halogenation
subclass of: end-of-chain chain shortening
subclass of: Class
  intersection of: Restriction
    on property: has specified product
    some values from: carboxylic acid
  intersection of: Restriction
    on property: has specified product
    some values from: halomethane
subclass of: Class
  intersection of: Restriction
    on property: has specified reactant
    some values from: elemental halogen
  intersection of: Restriction
    on property: has specified reactant
    some values from: methyl ketone
definition: Cleavage of methyl ketones (i.e. oxidative demethylation) with halogens (or hypohalites) in the presence of a base to give a carboxylic acid and haloform (trihalomethane).
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-16T11:10:42Z
has_obo_namespace: RXNO
has_related_synonym: Einhorn reaction
has_related_synonym: Lieben reaction
id: RXNO:0000689

Axiom
annotated source: haloform reaction
annotated property: definition
annotated target: Cleavage of methyl ketones (i.e. oxidative demethylation) with halogens (or hypohalites) in the presence of a base to give a carboxylic acid and haloform (trihalomethane).
database_cross_reference: https://en.wikipedia.org/wiki/Haloform_reaction
database_cross_reference: https://www.rsc.org/Merck-Index/reaction/r257/lieben%20iodoform%20reaction

Atherton-Todd reaction
type: Class
subclass of: halogenation
subclass of: functional group oxidation
subclass of: Class
  intersection of: Restriction
    on property: has specified reactant
    some values from: tetrachloromethane
  intersection of: Restriction
    on property: has specified reactant
    some values from: phosphonic ester
subclass of: Restriction
  on property: has specified product
  some values from: dialkyl phosphate
definition: The conversion of dialkyl phosphites (dialkyl phosphonates) to dialkyl chlorophosphates using tetrachloromethane and a base (usually a primary, secondary or tertiary amine).
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-16T12:05:47Z
has_obo_namespace: RXNO
has_related_synonym: AT reaction
id: RXNO:0000690
comment: Since the dialkyl chlorophosphates formed are often too reactive to be isolated, conversion to the corresponding phosphate or phosphoramidate occurs in the presence of a suitable nucleophile (e.g., alcohol or amine) after the actual Atherton-Todd reaction.

Axiom
annotated source: Atherton-Todd reaction
annotated property: definition
annotated target: The conversion of dialkyl phosphites (dialkyl phosphonates) to dialkyl chlorophosphates using tetrachloromethane and a base (usually a primary, secondary or tertiary amine).
database_cross_reference: https://doi.org/10.3762/bjoc.10.117
database_cross_reference: https://en.wikipedia.org/wiki/Atherton%E2%80%93Todd_reaction

Baeyer diarylmethane synthesis
type: Class
subclass of: molecular dehydration reaction
subclass of: molecular skeleton joining reaction
subclass of: Class
  intersection of: Restriction
    on property: has specified reactant
    some values from: aldehyde
  intersection of: Restriction
    on property: has specified reactant
    some values from: organic aromatic compound
subclass of: Restriction
  on property: has specified product
  some values from: diarylmethane
definition: Synthesis of diarylmethane derivatives using an aldehyde and an aromatic compound at low temperature in an acidic medium.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-16T12:54:23Z
has_obo_namespace: RXNO
id: RXNO:0000691
comment: A Friedel-Crafts type reaction proceeding via electrophilic aromatic substitution.

Axiom
annotated source: Baeyer diarylmethane synthesis
annotated property: definition
annotated target: Synthesis of diarylmethane derivatives using an aldehyde and an aromatic compound at low temperature in an acidic medium.
database_cross_reference: https://doi.org/10.1016/B978-0-08-096630-4.00412-8

silyl deprotection
type: Class
subclass of: hydroxy group deprotection
subclass of: Restriction
  on property: deprotects
  some values from: hydroxy group
subclass of: Restriction
  on property: has specified reactant
  some values from: silyl ether
definition: A hydroxyl group deprotection in which an silyl ether group is transformed into a hydroxy group.
creator: http://orcid.org/0000-0002-4378-6061
date: 2021-12-16T13:23:35Z
has_obo_namespace: RXNO
id: RXNO:0000692