RXNO is the name reaction ontology. It contains more than 500 classes representing organic reactions such as the Diels–Alder cyclization.
RXNO
16:12:2021 15:55
RXNO
1.4
definition
imported from
has_alternative_id
has_broad_synonym
database_cross_reference
has_exact_synonym
has_narrow_synonym
has_obo_format_version
has_obo_namespace
has_related_synonym
in_subset
RXNO
BFO:0000055
realizes
RXNO
BFO:0000057
has_participant
RXNO
BFO:0000077
has participant beginning to exist
RXNO
BFO:0000078
has participant ceasing to exist
RXNO
BFO:0000162
has disposition at all times
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.
RXNO
OBI:0000417
achieves_planned_objective
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.
obi:AR
obi:BP
obi:PPPBbranch
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.
RXNO
RXNO:0000416
can we chain 'has specified reactant' (RXNO:0000424) and has_part ?
protects
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.
https://orcid.org/0000-0001-5985-7429
If a reaction R deprotects a group G, then G is in the product where it wasn't in the reactant.
RXNO
RXNO:0000417
can we chain 'has specified product' (RXNO:0000423) and has_part ?
deprotects
If a reaction R deprotects a group G, then G is in the product where it wasn't in the reactant.
https://orcid.org/0000-0001-5985-7429
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.
RXNO
RXNO:0000423
The difference between this and OBI's has_specified_output is that it is necessary that the participant starts to exist during the process.
has specified product
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.
https://orcid.org/0000-0001-5985-7429
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.
RXNO
RXNO:0000424
The difference between this and OBI's has_specified_input is that it is necessary that the reactant ceases to exist during the process.
has specified reactant
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.
https://orcid.org/0000-0001-5985-7429
A relation between a planned reaction step and a molecular entity participating in that process that has_role catalyst ((CHEBI:35223).
RXNO
RXNO:0000425
has_catalyst
A relation between a planned reaction step and a molecular entity participating in that process that has_role catalyst ((CHEBI:35223).
https://orcid.org/0000-0001-5985-7429
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.
RXNO
RXNO:0000469
has_intermediate
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.
https://orcid.org/0000-0001-5985-7429
RXNO
has_part
has_part
RXNO
part_of
part_of
RXNO
BFO:0000015
process
RXNO
BFO:0000016
disposition
RXNO
CHEBI:13759
alkylamine
An alpha-oxyketone that has a hydroxy group as the alpha-oxy moiety.
http://purl.obolibrary.org/obo/chebi/205/chebi.owl
chebi_ontology
CHEBI:139588
alpha-hydroxy ketone
RXNO
CHEBI:15379
dioxygen
RXNO
CHEBI:15734
primary alcohol
An organic hydroxy compound that consists of benzene bearing a single hydroxy substituent. The parent of the class of phenols.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
CHEBI:14777
CHEBI:25966
CHEBI:43543
CHEBI:8071
chebi_ontology
CHEBI:15882
phenol
An azane that consists of a single nitrogen atom covelently bonded to three hydrogen atoms.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
CHEBI:13405
CHEBI:13406
CHEBI:13407
CHEBI:13771
CHEBI:22533
CHEBI:44269
CHEBI:44284
CHEBI:44404
CHEBI:7434
chebi_ontology
CHEBI:16134
ammonia
RXNO
CHEBI:16227
pyridine
RXNO
CHEBI:16240
hydrogen peroxide
Compounds having the structure RSR (R =/= H). Such compounds were once called thioethers.
CHEBI:13694
CHEBI:26960
CHEBI:9340
chebi_ontology
CHEBI:16385
organic sulfide
RXNO
CHEBI:16526
carbon dioxide
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
CHEBI:14137
CHEBI:23664
CHEBI:4486
chebi_ontology
CHEBI:16648
dialkyl phosphate
RXNO
CHEBI:16670
peptide
RXNO
CHEBI:16842
formaldehyde
RXNO
CHEBI:17087
ketone
A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
CHEBI:13281
CHEBI:23013
CHEBI:3282
CHEBI:41526
chebi_ontology
CHEBI:17245
carbon monoxide
An organosilicon compound that is benzene in which a hydrogen is replaced by a silyl group.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:172874
phenylsilane
RXNO
CHEBI:17478
aldehyde
A compound containing at least one carbon-halogen bond (where X is a halogen atom).
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
CHEBI:13444
CHEBI:36684
CHEBI:8767
chebi_ontology
CHEBI:17792
organohalogen compound
RXNO
CHEBI:17883
hydrogen chloride
An elemental molecule consisting of two trivalently-bonded nitrogen atoms.
0
N2
InChI=1S/N2/c1-2
IJGRMHOSHXDMSA-UHFFFAOYSA-N
28.01348
28.00615
N#N
CHEBI:13388
CHEBI:14660
CHEBI:25365
CHEBI:43128
CHEBI:7593
CAS:7727-37-9
Drug_Central:4251
Gmelin:150
HMDB:HMDB0001371
KEGG:C00697
KEGG:D00083
MetaCyc:NITROGEN-MOLECULE
PDBeChem:HDZ
PMID:18334638
PMID:22237545
Reaxys:15940095
Wikipedia:Nitrogen
dinitrogen
chebi_ontology
N#N
N2
Nitrogen
molecular nitrogen
CHEBI:17997
dinitrogen
CAS:7727-37-9
NIST Chemistry WebBook
Drug_Central:4251
DrugCentral
Gmelin:150
Gmelin
PMID:18334638
Europe PMC
PMID:22237545
Europe PMC
Reaxys:15940095
Reaxys
dinitrogen
IUPAC
N#N
ChEBI
N2
IUPAC
N2
KEGG_COMPOUND
N2
UniProt
Nitrogen
KEGG_COMPOUND
molecular nitrogen
ChEBI
CAS:7727-37-9
ChemIDplus
CAS:7727-37-9
KEGG COMPOUND
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
CHEBI:13368
CHEBI:37140
CHEBI:5599
chebi_ontology
CHEBI:18140
hydrogen halide
A manganese group element atom that has formula Mn.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
CHEBI:13382
CHEBI:25153
CHEBI:6681
chebi_ontology
CHEBI:18291
manganese atom
An acyclic branched or unbranched hydrocarbon having the general formula CnH2n+2, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms.
0
CH3R
15.035
15.02348
C[*]
CHEBI:13435
CHEBI:22317
CHEBI:2576
KEGG:C01371
Alkane
alkane
alkanes
chebi_ontology
Alkan
RH
alcane
alcanes
alcano
alcanos
an alkane
CHEBI:18310
alkane
Alkane
KEGG_COMPOUND
alkane
IUPAC
alkanes
IUPAC
Alkan
ChEBI
RH
KEGG_COMPOUND
alcane
IUPAC
alcanes
IUPAC
alcano
IUPAC
alcanos
IUPAC
an alkane
UniProt
RXNO
CHEBI:18379
nitrile
RXNO
CHEBI:22213
acridines
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:22324
alkyl phosphate
Acyclic branched or unbranched hydrocarbons having a carbon-carbon triple bond and the general formula CnH2n-2, RC#CR.
chebi_ontology
CHEBI:22339
alkyne
RXNO
CHEBI:33855
arenecarbaldehyde
RXNO
CHEBI:22680
azide
RXNO
CHEBI:22698
benzaldehydes
Any benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:22712
benzenes
RXNO
CHEBI:22715
benzimidazoles
RXNO
CHEBI:22929
bromoalkane
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:23014
carbon oxide
0
CO
28.01010
27.99491
O=C(*)*
carbonyl
carbonyl group
chebi_ontology
>C=O
CHEBI:23019
carbonyl group
carbonyl
IUPAC
carbonyl group
ChEBI
carbonyl group
UniProt
>C=O
IUPAC
RXNO
CHEBI:23086
chalcones
RXNO
CHEBI:23128
chloroalkane
RXNO
CHEBI:23252
cinnamic acids
RXNO
CHEBI:23367
molecular entity
Salts and C-organyl derivatives of hydrogen cyanide, HC#N.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:23424
cyanides
RXNO
CHEBI:24043
flavones
RXNO
CHEBI:24079
formamides
RXNO
CHEBI:24129
furans
RXNO
CHEBI:24431
chemical entity
RXNO
CHEBI:24433
group
RXNO
CHEBI:24469
haloalkane
A compound derived from a hydrocarbon by replacing a hydrogen atom with a halogen atom.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:24472
halohydrocarbon
RXNO
CHEBI:24828
indoles
RXNO
CHEBI:25000
lactone
Any member of the class of toluenes bearing one or more nitro substituents on the benzene ring.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:25566
nitrotoluene
RXNO
CHEBI:25698
ether
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:25703
organic phosphate
A compound having bonds between one or more metal atoms and one or more carbon atoms of an organyl group.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:25707
organometallic compound
RXNO
CHEBI:25710
organophosphorus compound
An organosilicon compound is a compound containing at least one carbon-silicon bond.
organosilicon compound
chebi_ontology
organosilicon compounds
silicoorganic compounds
CHEBI:25713
organosilicon compound
organosilicon compound
ChEBI
organosilicon compounds
ChEBI
silicoorganic compounds
ChEBI
RXNO
CHEBI:25717
organotin compound
RXNO
CHEBI:25750
oxime
RXNO
CHEBI:25996
phenylhydrazine
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.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:2634
amidine
http://purl.obolibrary.org/obo/chebi/205/chebi.owl
chebi_ontology
CHEBI:26407
pyrans
RXNO
CHEBI:26410
pyrazoles
RXNO
CHEBI:26421
pyridines
RXNO
CHEBI:26455
pyrroles
RXNO
CHEBI:26513
quinolines
A molecular entity possessing an unpaired electron.
http://purl.obolibrary.org/obo/chebi/205/chebi.owl
chebi_ontology
CHEBI:26519
radical
RXNO
CHEBI:26588
triazines
RXNO
CHEBI:26708
sodium atom
RXNO
CHEBI:26878
tertiary alcohol
RXNO
CHEBI:26961
thiophenes
Any member of the class of benzenes that is a substituted benzene in which the substituents include one (and only one) methyl group.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:27024
toluenes
RXNO
CHEBI:27081
transition element atom
RXNO
CHEBI:27363
zinc atom
RXNO
CHEBI:27385
tetrachloromethane
RXNO
CHEBI:27539
isatin
RXNO
CHEBI:278547
sodium azide
RXNO
CHEBI:28112
nickel atom
RXNO
CHEBI:28659
phosphorus atom
RXNO
CHEBI:28694
copper atom
RXNO
CHEBI:28802
flavonols
RXNO
CHEBI:29224
dibromine
An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.
CHEBI:13443
CHEBI:13696
CHEBI:17366
CHEBI:26969
CHEBI:8766
CHEBI:9556
chebi_ontology
CHEBI:29256
thiol
A sulfur hydride that has formula HS.
chebi_ontology
CHEBI:29312
sulfanyl
RXNO
CHEBI:29785
nitro group
0
H2N2
InChI=1S/H2N2/c1-2/h1-2H
RAABOESOVLLHRU-UHFFFAOYSA-N
30.02936
30.02180
N=N
CAS:3618-05-1
KEGG:C05360
diazene
chebi_ontology
Diimide
HN=NH
CHEBI:30096
diazene
CAS:3618-05-1
ChemIDplus
CAS:3618-05-1
NIST Chemistry WebBook
diazene
IUPAC
Diimide
NIST_Chemistry_WebBook
HN=NH
IUPAC
RXNO
CHEBI:30879
alcohol
An indolinone carrying an oxo group at position 2.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:31697
indolin-2-one
RXNO
CHEBI:32816
pyruvic acid
RXNO
CHEBI:32863
secondary amine
RXNO
CHEBI:32876
tertiary amine
RXNO
CHEBI:32877
primary amine
RXNO
CHEBI:32878
alkene
RXNO
CHEBI:32952
amine
RXNO
CHEBI:32955
epoxide
RXNO
CHEBI:32988
amide
RXNO
CHEBI:33250
atom
RXNO
CHEBI:33256
primary amide
A molecular entity all atoms of which have the same atomic number.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:33259
elemental molecular entity
RXNO
CHEBI:33308
carboxylic ester
RXNO
CHEBI:33338
aryl group
RXNO
CHEBI:33341
titanium atom
RXNO
CHEBI:33363
palladium atom
RXNO
CHEBI:33364
platinum atom
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:33403
elemental sulfur
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:33434
elemental halogen
RXNO
CHEBI:33521
metal atom
RXNO
CHEBI:33575
carboxylic acid
RXNO
CHEBI:33595
cyclic compound
A cyclic compound having as ring members atoms of the same element only.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:33597
homocyclic compound
A homocyclic compound in which all of the ring members are carbon atoms.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:33598
carbocyclic compound
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:33635
polycyclic compound
RXNO
CHEBI:33641
olefin
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.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:33655
aromatic compound
RXNO
CHEBI:33658
arene
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:33659
organic aromatic compound
A polycyclic compound in which at least one of the rings contains at least one non-carbon atom.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:33671
heteropolycyclic compound
RXNO
CHEBI:33822
organic hydroxy compound
RXNO
CHEBI:33823
enol
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:33836
benzenoid aromatic compound
RXNO
CHEBI:33839
macromolecule
A monocyclic aromatic hydrocarbon.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:33847
monocyclic arene
A polycyclic aromatic hydrocarbon.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:33848
polycyclic arene
RXNO
CHEBI:33853
phenols
RXNO
CHEBI:33860
aromatic amine
RXNO
CHEBI:35255
chloroform
RXNO
CHEBI:35293
fused compound
RXNO
CHEBI:35352
organonitrogen compound
The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:35353
isocyanide
RXNO
CHEBI:35403
chromium coordination entity
RXNO
CHEBI:35562
1,2,3-triazole
RXNO
CHEBI:35636
carboximides
RXNO
CHEBI:35681
secondary alcohol
RXNO
CHEBI:35689
tetrazoles
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.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
CHEBI:23960
CHEBI:4859
chebi_ontology
CHEBI:35701
ester
RXNO
CHEBI:35715
nitro compound
RXNO
CHEBI:35873
carboxylic anhydride
RXNO
CHEBI:35886
tertiary phosphine
RXNO
CHEBI:36587
carbonyl compound
RXNO
CHEBI:36601
triphenylphosphane oxide
RXNO
CHEBI:36605
phthalic anhydride
RXNO
CHEBI:36606
acid anhydride
RXNO
CHEBI:36687
acyl chloride
RXNO
CHEBI:36823
pseudohalo group
http://purl.obolibrary.org/obo/chebi/205/chebi.owl
chebi_ontology
CHEBI:36871
inorganic radical
http://purl.obolibrary.org/obo/chebi/205/chebi.owl
chebi_ontology
CHEBI:36872
organic radical
RXNO
CHEBI:36963
organooxygen compound
RXNO
CHEBI:37148
bromoarene
Any heteroatomic molecular entity that is a chemical compound of halogen with other chemical elements.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:37578
halide
RXNO
CHEBI:37579
acyl halide
RXNO
CHEBI:37592
organic phosphonate
RXNO
CHEBI:37602
allenes
RXNO
CHEBI:37613
cyclohexadiene
RXNO
CHEBI:37622
carboxamide
A phosphonic acid derivative in which one or both OH groups have been esterified.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
CHEBI:26068
CHEBI:4861
chebi_ontology
CHEBI:37735
phosphonic ester
RXNO
CHEBI:37757
iodoalkane
Any of a class of cyclic chemical compounds that contain an unsaturated six-membered ring with one ring oxygen atom and an oxo substituent.
http://purl.obolibrary.org/obo/chebi/205/chebi.owl
chebi_ontology
CHEBI:37963
pyranone
Any organonitrogen compound containing a cyclic component with nitrogen and at least one other element as ring member atoms.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
RXNO
chebi_ontology
CHEBI:38101
organonitrogen heterocyclic compound
RXNO
CHEBI:38104
oxacycle
thiacycle
RXNO
CHEBI:38106
I think this is the same as a thiacycle but need to check.
organosulfur heterocyclic compound
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
CHEBI:25429
CHEBI:38075
chebi_ontology
CHEBI:38166
organic heteropolycyclic compound
RXNO
CHEBI:38269
boronic acids
RXNO
CHEBI:38597
triazole
RXNO
CHEBI:38757
isoflavones
RXNO
CHEBI:38784
oxetanes
A monocyclic arene that is benzene substituted with one or more alkyl groups.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:38976
alkylbenzene
RXNO
CHEBI:39141
Brønsted acid
RXNO
CHEBI:39142
Brønsted base
RXNO
CHEBI:39143
Lewis acid
RXNO
CHEBI:39144
Lewis base
A haloalkane that is methane in which one (or more) of the hydrogens have been replaced by a halogen atom/halogen atoms.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:39279
halomethane
RXNO
CHEBI:39447
pyrimidines
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.
http://purl.obolibrary.org/obo/chebi/205/chebi.owl
chebi_ontology
CHEBI:39477
aminoxyls
RXNO
CHEBI:42485
formyl group
RXNO
CHEBI:43176
hydroxy group
A dithiol that is propane substituted by thiol groups at positions 1 ans 3.
http://purl.obolibrary.org/obo/chebi/200/chebi.owl
chebi_ontology
CHEBI:44864
propane-1,3-dithiol
RXNO
CHEBI:46882
amino group
RXNO
CHEBI:46883
carboxy group
RXNO
CHEBI:47266
hydrogen bromide
RXNO
CHEBI:47875
tetrabromomethane
Ethers ROR' where R has a double bond adjacent to the oxygen of the ether linkage.
http://purl.obolibrary.org/obo/chebi/205/chebi.owl
chebi_ontology
CHEBI:47985
enol ether
Enol ethers ROR' where R' has the structure SiR''R'''R''''.
http://purl.obolibrary.org/obo/chebi/205/chebi.owl
chebi_ontology
CHEBI:47986
silyl enol ether
Ethers ROR' where R' has the structure SiR''R'''R''''.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:47988
silyl ether
RXNO
CHEBI:48420
chromium trioxide
RXNO
CHEBI:48513
carbazoles
An azole in which the five-membered heterocyclic aromatic skeleton contains a N atom and one S atom.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:48901
thiazoles
RXNO
CHEBI:49553
copper(II) chloride
A compound formally derived from ammonia by replacing one, two or three hydrogen atoms by organyl groups.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:50047
organic amino compound
RXNO
CHEBI:50075
dihydropyridine
http://purl.obolibrary.org/obo/chebi/205/chebi.owl
CHEBI:24671
CHEBI:5798
chebi_ontology
CHEBI:50413
hydroxyaldehyde
RXNO
CHEBI:50784
pivalate ester
A compound derived from an arene by replacing a hydrogen atom with a halogen atom.
http://purl.obolibrary.org/obo/chebi/200/chebi.owl
RXNO
chebi_ontology
CHEBI:50887
haloarene
RXNO
CHEBI:50888
fluoroarene
A salt or ester of boronic acid.
http://purl.obolibrary.org/obo/chebi/200/chebi.owl
chebi_ontology
CHEBI:50978
boronate
RXNO
CHEBI:51080
nitrate ester
RXNO
CHEBI:51142
amino groups
RXNO
CHEBI:51154
phosphonium ylide
A compound containing at least one carbon-lithium bond.
http://purl.obolibrary.org/obo/chebi/200/chebi.owl
chebi_ontology
CHEBI:51186
organolithium compound
A compound containing at least one carbon-magnesium bond.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:51187
organomagnesium compound
RXNO
CHEBI:51236
organomagnesium halide
A compound of general formula RC(=O)SR'. Compare with thionoester, RC(=S)OR'.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:51277
thioester
RXNO
CHEBI:51454
cyclopropanes
An organolithium compound where an alkyl group is bound to a lithium atom.
http://purl.obolibrary.org/obo/chebi/200/chebi.owl
chebi_ontology
CHEBI:51462
alkyllithium compound
An alkyllithium compound that has formula C4H9Li.
http://purl.obolibrary.org/obo/chebi/200/chebi.owl
chebi_ontology
CHEBI:51469
butyllithium
A compound containing at least one carbon-zinc bond.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:51494
organozinc compound
Any compound containing two aryl groups connected by a single C atom.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:51614
diarylmethane
RXNO
CHEBI:51721
alpha,beta-unsaturated ketone
A haloketone in which the halogen and oxo substituents are on adjacent carbon atoms.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:51839
alpha-haloketone
RXNO
CHEBI:51849
beta-ketoester
A ketone of formula RC(=O)CH3 (R =/= H).
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:51867
methyl ketone
RXNO
CHEBI:51929
arylacetylene
RXNO
CHEBI:52094
peroxy acid
A compound with the general formula R2C=O (R=/=H) where one or more of the R groups contains an oxy (-O-) group.
http://purl.obolibrary.org/obo/chebi/205/chebi.owl
chebi_ontology
CHEBI:52395
oxyketone
RXNO
CHEBI:53212
isocyanates
RXNO
CHEBI:53434
palladium(II) chloride
RXNO
CHEBI:55380
beta-hydroxy ketone
A compound having the general formula RR'C(OH)OR'' (R'' =/= H).
0
CH2O2R2
46.025
46.00548
Hemiacetal
hemiacetals
chebi_ontology
hemiacetals
CHEBI:5653
hemiacetal
Hemiacetal
KEGG_COMPOUND
hemiacetals
IUPAC
hemiacetals
ChEBI
RXNO
CHEBI:5686
heterocyclic compound
RXNO
CHEBI:59656
phosphine oxide
An organooxygen compound having the structure RR'C(OR'')(OR''') (R'', R''' =/= H). Mixed acetals have R'' and R''' groups which differ.
chebi_ontology
acetals
CHEBI:59769
acetal
acetals
ChEBI
RXNO
CHEBI:59831
enyne
A chemical substance is a portion of matter of constant composition, composed of molecular entities of the same type or of different types.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:59999
chemical substance
A mixture is a chemical substance composed of multiple molecules, at least two of which are of a different kind.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:60004
mixture
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..
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:60027
polymer
An organic phosphonate containing a C-PO(OH)2 or C-PO(OR)2 group (where R = alkyl group).
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
CHEBI:2591
chebi_ontology
CHEBI:60983
alkylphosphonate
An organic phosphonate of formula (RO)2P(=O)-CR2-NR2; R can be H.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:61111
aminophosphonate
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.
http://purl.obolibrary.org/obo/chebi/206/chebi.owl
chebi_ontology
CHEBI:68452
azole
RXNO
CHEBI:72695
organic molecule
RXNO
CHEBI:73474
acetylenic compound
RXNO
CHEBI:73477
terminal acetylenic compound
RXNO
IAO:0000005
objective specification
RXNO
IAO:0000030
information content entity
Formation of a covalent bond between a substrate and a formyl group.
formylation
RXNO
MOP:0000003
formylation
Formation of a covalent bond between a substrate and a formyl group.
RSC:xp
Formation of a covalent bond between a substrate and an silyl group.
silylation
RXNO
MOP:0000339
has_participant: CHEBI:33478
silylation
Formation of a covalent bond between a substrate and an silyl group.
RSC:xp
RXNO
MOP:0000364
methylation
Formation of a covalent bond between a substrate and an alkyl group.
alkylation
RXNO
MOP:0000369
has_participant: CHEBI:22323
alkylation
Formation of a covalent bond between a substrate and an alkyl group.
RSC:xp
Formation of a covalent bond between a substrate and a hydrocarbyl group.
hydrocarbylation
RXNO
MOP:0000410
has_participant: CHEBI:33248
hydrocarbylation
Formation of a covalent bond between a substrate and a hydrocarbyl group.
RSC:xp
Formation of a covalent bond between a substrate and an aryl group.
arylation
RXNO
MOP:0000411
arylation
Formation of a covalent bond between a substrate and an aryl group.
RSC:xp
Formation of a covalent bond between a substrate and an allyl group.
allylation
RXNO
MOP:0000422
has_participant: CHEBI:30361
allylation
Formation of a covalent bond between a substrate and an allyl group.
RSC:xp
Formation of a covalent bond between a substrate and an organyl group.
organylation
RXNO
MOP:0000458
has_participant: CHEBI:33249
organylation
Formation of a covalent bond between a substrate and an organyl group.
RSC:xp
Formation of a covalent bond between a substrate and an acyl group.
acylation
RXNO
MOP:0000479
has_participant: CHEBI:22221
acylation
Formation of a covalent bond between a substrate and an acyl group.
RSC:xp
true
Formation of a covalent bond between a substrate and a sulfonyl group.
MOP:0000524
sulfonylation
RXNO
MOP:0000539
has_participant: CHEBI:51100; has_participant: CHEBI:29825
sulfonylation
Formation of a covalent bond between a substrate and a sulfonyl group.
RSC:xp
A process in which at least one of the participants is a molecule.
RXNO
MOP:0000543
TODO: needs work, formal definition, etc.
molecular process
A process in which at least one of the participants is a molecule.
https://orcid.org/0000-0001-5985-7429
Formation of a covalent bond between a substrate and a halo group.
RXNO
MOP:0000550
has_participant: CHEBI:47854
halogenation
Formation of a covalent bond between a substrate and a halo group.
RSC:xp
Formation of a covalent bond between a substrate and an imino group.
RXNO
MOP:0000555
has_participant: CHEBI:29342
imination
Formation of a covalent bond between a substrate and an imino group.
RSC:xp
Formation of a covalent bond between a substrate and a nitro group.
RXNO
MOP:0000556
nitration
Formation of a covalent bond between a substrate and a nitro group.
RSC:xp
Formation of a ring in a molecule from a chain by formation of a new bond.
cyclisation
RXNO
MOP:0000561
cyclization
Formation of a ring in a molecule from a chain by formation of a new bond.
AU:C01494
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.
RXNO:0000314
RXNO
MOP:0000562
cycloaddition
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.
AU:C01496
A cycloaddition in which each participant contributes two electrons to the transformation of reactants to products.
RXNO
MOP:0000563
[2+2] cycloaddition
A cycloaddition in which each participant contributes two electrons to the transformation of reactants to products.
https://orcid.org/0000-0001-5985-7429
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.
cycloreversion
retro-addition
retrocycloaddition
RXNO
MOP:0000564
cycloelimination
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.
AU:C01496
AU:C01501
cycloreversion
AU:C01506
retrocycloaddition
AU:R05372
A cycloaddition in which one participant contributes four electrons and the other participant contributes two electrons to the transformation of reactants to products.
RXNO
MOP:0000565
[4+2] cycloaddition
A cycloaddition in which one participant contributes four electrons and the other participant contributes two electrons to the transformation of reactants to products.
https://orcid.org/0000-0001-5985-7429
Formation of a covalent bond between a substrate and a group.
batchelorc
2009-04-22T10:01:32Z
RXNO
MOP:0000566
formation of covalent bond with group
Formation of a covalent bond between a substrate and a group.
https://orcid.org/0000-0001-5985-7429
Breaking of a covalent bond between a substrate and a group.
batchelorc
2009-04-30T02:24:32Z
RXNO
MOP:0000567
breaking of covalent bond with group
Breaking of a covalent bond between a substrate and a group.
https://orcid.org/0000-0001-5985-7429
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.
batchelorc
2009-06-01T06:01:47Z
de-electronation
RXNO
MOP:0000568
oxidation
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.
AU:O04362
The complete transfer of one or more electrons to a molecular entity.
batchelorc
2009-06-01T06:04:18Z
electronation
RXNO
MOP:0000569
reduction
The complete transfer of one or more electrons to a molecular entity.
AU:R05222
The transfer of an electron to a molecular entity, resulting in a molecular entity of increased negative charge.
batchelorc
2009-06-01T06:06:19Z
RXNO
MOP:0000570
electron attachment
The transfer of an electron to a molecular entity, resulting in a molecular entity of increased negative charge.
AU:E01979
A reduction in which an aldehyde is reduced to form a primary alcohol.
batchelorc
2009-06-01T06:07:02Z
RXNO
MOP:0000571
aldehyde reduction
A reduction in which an aldehyde is reduced to form a primary alcohol.
https://orcid.org/0000-0001-5985-7429
An oxidation process where an alcohol is transformed into a carbonyl compound.
batchelorc
2009-06-01T06:10:35Z
RXNO
MOP:0000572
alcohol oxidation
An oxidation process where an alcohol is transformed into a carbonyl compound.
https://orcid.org/0000-0001-5985-7429
An oxidation process where a primary alcohol is transformed into an aldehyde.
batchelorc
2009-06-01T06:10:59Z
RXNO
MOP:0000573
primary alcohol oxidation to aldehyde
An oxidation process where a primary alcohol is transformed into an aldehyde.
https://orcid.org/0000-0001-5985-7429
An oxidation process where a secondary alcohol is transformed into a ketone.
batchelorc
2009-06-01T06:11:31Z
RXNO
MOP:0000574
secondary alcohol oxidation to ketone
An oxidation process where a secondary alcohol is transformed into a ketone.
https://orcid.org/0000-0001-5985-7429
An oxidation process where an amine is transformed into an imine.
batchelorc
2009-06-01T06:15:40Z
RXNO
MOP:0000575
amine oxidation
An oxidation process where an amine is transformed into an imine.
https://orcid.org/0000-0001-5985-7429
A reduction process where an imine is transformed into an amine.
batchelorc
2009-06-01T06:19:21Z
RXNO
MOP:0000576
imine reduction
A reduction process where an imine is transformed into an amine.
https://orcid.org/0000-0001-5985-7429
A reduction process where the oxidation state carbonyl carbon in the ester functionality is reduced.
batchelorc
2009-06-02T05:30:48Z
reduction of ester
RXNO
MOP:0000577
ester reduction
A reduction process where the oxidation state carbonyl carbon in the ester functionality is reduced.
https://orcid.org/0000-0001-5985-7429
An ester reduction where the product is the corresponding aldehyde.
batchelorc
2009-06-02T05:31:49Z
reduction of ester to aldehyde
reduction of esters to aldehyde
RXNO
MOP:0000578
ester reduction to aldehyde
An ester reduction where the product is the corresponding aldehyde.
https://orcid.org/0000-0001-5985-7429
An ester reduction where the product is the corresponding primary alcohol.
batchelorc
2009-06-02T05:32:37Z
reduction of ester to primary alcohol
reduction of esters to primary alcohol
RXNO
MOP:0000579
ester reduction to primary alcohol
An ester reduction where the product is the corresponding primary alcohol.
https://orcid.org/0000-0001-5985-7429
A reduction process where a ketone is reduced to a secondary alcohol.
batchelorc
2009-06-02T05:35:42Z
reduction of ketone
reduction of ketones
RXNO
MOP:0000580
ketone reduction
A reduction process where a ketone is reduced to a secondary alcohol.
https://orcid.org/0000-0001-5985-7429
An oxidation process where the oxidation state of at least one doubly-bonded carbon atom increases.
batchelorc
2009-06-02T05:45:30Z
olefin oxidation
RXNO
MOP:0000581
alkene oxidation
An oxidation process where the oxidation state of at least one doubly-bonded carbon atom increases.
https://orcid.org/0000-0001-5985-7429
An alkene oxidation where the product is the corresponding 1,2-diol.
batchelorc
2009-06-02T05:46:52Z
alkene oxidation to glycol
oxidation of alkene to 1,2-diol
oxidation of alkenes to 1,2-diol
RXNO
MOP:0000582
alkene oxidation to 1,2-diol
An alkene oxidation where the product is the corresponding 1,2-diol.
https://orcid.org/0000-0001-5985-7429
An alkene oxidation where the reagent is ozone and the product is the corresponding ozonide.
batchelorc
2009-06-02T05:48:42Z
ozonolysis of alkene
ozonolysis of alkenes
RXNO
MOP:0000583
alkene ozonolysis
An alkene oxidation where the reagent is ozone and the product is the corresponding ozonide.
https://orcid.org/0000-0001-5985-7429
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.
batchelorc
2009-06-02T06:02:46Z
RXNO
MOP:0000584
primary alkene oxidation to carboxylic acid and carbon dioxide
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.
https://orcid.org/0000-0001-5985-7429
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.
batchelorc
2009-06-02T06:04:14Z
RXNO
MOP:0000585
tertiary alkene oxidation to carboxylic acid and ketone
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.
https://orcid.org/0000-0001-5985-7429
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.
batchelorc
2009-06-02T06:06:23Z
RXNO
MOP:0000586
secondary, non-terminal alkene oxidation to aldehydes
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.
https://orcid.org/0000-0001-5985-7429
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.
batchelorc
2009-06-02T06:07:44Z
RXNO
MOP:0000587
secondary terminal alkene oxidation to ketone and carbon dioxide
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.
https://orcid.org/0000-0001-5985-7429
An alkene oxidation process where the reactant is a quaternary alkene and the products are the corresponding ketones.
batchelorc
2009-06-02T06:09:24Z
RXNO
MOP:0000588
quaternary alkene oxidation to ketones
An alkene oxidation process where the reactant is a quaternary alkene and the products are the corresponding ketones.
https://orcid.org/0000-0001-5985-7429
A reduction process that involves addition of hydrogen atoms across a double bond.
batchelorc
2009-06-05T04:53:34Z
RXNO
MOP:0000589
hydrogenation
A reduction process that involves addition of hydrogen atoms across a double bond.
https://orcid.org/0000-0001-5985-7429
Formation of a covalent bond between a substrate and a pseudohalo group.
RXNO
MOP:0000596
pseudohalogenation
Formation of a covalent bond between a substrate and a pseudohalo group.
RSC:xp
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.
batchelorc
2009-09-16T11:11:24Z
RXNO
MOP:0000618
solvolysis
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.
AU:S05762
https://orcid.org/0000-0001-5985-7429
A solvolysis reaction where the solvent material is water.
batchelorc
2009-09-16T11:13:21Z
RXNO
MOP:0000619
hydrolysis
A solvolysis reaction where the solvent material is water.
https://orcid.org/0000-0001-5985-7429
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.
batchelorc
2009-09-16T11:30:32Z
RXNO:0000315
RXNO
MOP:0000627
condensation reaction
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.
AU:C01238
A condensation reaction where the small molecule produced is water.
batchelorc
2009-09-16T11:32:33Z
RXNO
MOP:0000628
molecular dehydration reaction
A condensation reaction where the small molecule produced is water.
https://orcid.org/0000-0001-5985-7429
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.
MOP:0000642
addition reaction
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.
https://doi.org/10.1351/goldbook.A00133
Formation of a covalent bond between a substrate and an amino group.
RXNO
MOP:0000650
amination
Formation of a covalent bond between a substrate and an amino group.
https://orcid.org/0000-0001-5985-7429
A molecular process where two groups are lost with concomitant formation of an unsaturation in the molecule or formation of a new ring.
RXNO
MOP:0000656
elimination reaction
A molecular process where two groups are lost with concomitant formation of an unsaturation in the molecule or formation of a new ring.
doi:10.1351/goldbook.E02038
A cyclisation that results in the formation of an epoxide.
RXNO
MOP:0000671
epoxidation
A cyclisation that results in the formation of an epoxide.
https://orcid.org/0000-0001-5985-7429
An oxidation process where the oxidation state of at least one sulfur atom increases.
RXNO
MOP:0000705
oxidation at sulfur
An oxidation process where the oxidation state of at least one sulfur atom increases.
https://orcid.org/0000-0001-5985-7429
An oxidation process where the oxidation state of at least one nitrogen atom increases.
RXNO
MOP:0000706
oxidation at nitrogen
An oxidation process where the oxidation state of at least one nitrogen atom increases.
https://orcid.org/0000-0001-5985-7429
A formal account of the degree of oxidation of an atom.
http://goldbook.iupac.org/O04365.html
RXNO
MOP:0000712
It turns out to be formally defined, which makes our definitions a bit poor.
oxidation state
A formal account of the degree of oxidation of an atom.
https://orcid.org/0000-0001-5985-7429
Formation of a covalent bond between a molecule and a carboxy group.
RXNO
MOP:0000713
carboxylation
Formation of a covalent bond between a molecule and a carboxy group.
RSC:xp
Oxidation of a carbonyl group to an alkyne.
RXNO
MOP:0000714
carbonyl oxidation to alkyne
Oxidation of a carbonyl group to an alkyne.
https://orcid.org/0000-0001-5985-7429
A cycloaddition in which one participant contributes three electrons and the other participant contributes two electrons to the transformation of reactants to products.
RXNO
MOP:0000715
[3+2] cycloaddition
A cycloaddition in which one participant contributes three electrons and the other participant contributes two electrons to the transformation of reactants to products.
https://orcid.org/0000-0001-5985-7429
Molecular process in which an aldehyde or ketone tautomerises to form an enol.
enolization
RXNO
MOP:0000716
enolisation
Molecular process in which an aldehyde or ketone tautomerises to form an enol.
https://orcid.org/0000-0001-5985-7429
Disposition that is realised in the process of enolisation
RXNO
MOP:0000717
enolisability
Disposition that is realised in the process of enolisation
https://orcid.org/0000-0001-5985-7429
A carbonyl compound that bears the disposition to be enolised.
RXNO
MOP:0000718
this surely belongs in ChEBI but put it here pro tem
enolisable carbonyl compound
A carbonyl compound that bears the disposition to be enolised.
https://orcid.org/0000-0001-5985-7429
Breaking of a covalent bond between an alkyl group and an oxygen atom.
RXNO
MOP:0000719
O-dealkylation
Breaking of a covalent bond between an alkyl group and an oxygen atom.
RSC:xp
A cycloaddition in which two participants contribute two electrons and the other participant contributes one electron to the transformation of reactants to products.
RXNO
MOP:0000720
[2+2+1] cycloaddition
A cycloaddition in which two participants contribute two electrons and the other participant contributes one electron to the transformation of reactants to products.
https://orcid.org/0000-0001-5985-7429
RXNO:0000027
RXNO
MOP:0000721
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.
[3,3]-sigmatropic rearrangement
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.
batchelorc
2014-03-05T10:00:00Z
RXNO
MOP:0000722
decarboxylative condensation
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.
RSC:xp
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.
batchelorc
2014-03-05T10:00:00Z
RXNO
MOP:0000723
deethanolative condensation
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.
RSC:xp
batchelorc
2014-04-09T10:00:00Z
RXNO
MOP:0000730
Brønsted acid catalysis
batchelorc
2014-04-09T10:00:00Z
RXNO
MOP:0000731
base catalysis
batchelorc
2014-04-09T10:00:00Z
RXNO
MOP:0000732
hydron donation
batchelorc
2014-04-09T10:00:00Z
RXNO
MOP:0000733
accepting an electron pair in Lewis adduct formation
batchelorc
2014-04-09T10:00:00Z
RXNO
MOP:0000734
Lewis acid catalysis
batchelorc
2014-04-09T10:00:00Z
RXNO
MOP:0000735
Lewis base catalysis
batchelorc
2014-04-09T10:00:00Z
RXNO
MOP:0000736
Brønsted base catalysis
batchelorc
2014-04-09T10:00:00Z
RXNO
MOP:0000737
accepting a hydron
batchelorc
2014-04-09T10:00:00Z
RXNO
MOP:0000738
electron pair donation in Lewis adduct formation
RXNO
MOP:0000739
Lewis adduct formation
Catalysis of a reaction where the catalyst either donates a hydron or accepts an electron pair.
RXNO
MOP:0000740
acid catalysis
Catalysis of a reaction where the catalyst either donates a hydron or accepts an electron pair.
https://orcid.org/0000-0001-5985-7429
A reaction in which one singly-bonded group, but not the hydrogen atom, is replaced by another singly-bonded group.
RXNO:0000019
RXNO
MOP:0000790
The Gold Book says hydrogen atoms count, but this differs from everyone's intuition. See http://goldbook.iupac.org/S06078.html
substitution reaction
A reaction in which one singly-bonded group, but not the hydrogen atom, is replaced by another singly-bonded group.
https://orcid.org/0000-0001-5985-7429
A substitution reaction in which one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent.
RXNO:0000020
RXNO
MOP:0000791
aromatic substitution
A substitution reaction in which one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent.
https://orcid.org/0000-0001-5985-7429
A substitution reaction in an allylic system with concomitant migration of the allyl double bond.
RXNO:0000033
RXNO
MOP:0000792
allylic rearrangement
A substitution reaction in an allylic system with concomitant migration of the allyl double bond.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A substitution reaction where the reactive centre is a nitrogen atom.
RXNO:0000319
RXNO
MOP:0000793
N-substitution
A substitution reaction where the reactive centre is a nitrogen atom.
https://orcid.org/0000-0001-5985-7429
A substitution reaction where the reactive centre is an oxygen atom.
RXNO:0000318
NAMERXN:1.7
RXNO
MOP:0000794
O-substitution
A substitution reaction where the reactive centre is an oxygen atom.
https://orcid.org/0000-0001-5985-7429
A substitution reaction where the reactive centre is a sulfur atom.
batchelorc
2012-03-22T12:22:59Z
RXNO:0000336
NAMERXN:1.8
RXNO
MOP:0000795
S-substitution
A substitution reaction where the reactive centre is a sulfur atom.
https://orcid.org/0000-0001-5985-7429
Formation of a covalent bond with a group where the free valence is on a nitrogen centre.
RXNO
MOP:0000802
formation of covalent bond with nitrogen centre
Formation of a covalent bond with a group where the free valence is on a nitrogen centre.
https://orcid.org/0000-0001-5985-7429
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.
RXNO
MOP:0000825
dealcoholative condensation
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.
https://orcid.org/0000-0001-5985-7429
A disposition which is realised in a [4+2] reaction with a double-bonded system.
http://goldbook.iupac.org/D01700.html
RXNO
MOP:0000826
dienophilicity
A disposition which is realised in a [4+2] reaction with a double-bonded system.
https://orcid.org/0000-0001-5985-7429
Breaking of a covalent bond between an alkyl group and a substrate.
RXNO
MOP:0001369
dealkylation
Breaking of a covalent bond between an alkyl group and a substrate.
RSC:xp
Breaking of a covalent bond between a substrate and an organyl group.
RXNO
MOP:0001458
has_participant: CHEBI:33249
deorganylation
Breaking of a covalent bond between a substrate and an organyl group.
RSC:xp
Breaking of a covalent bond between a substrate and a halo group.
RXNO
MOP:0001550
has_participant: CHEBI:47854
dehalogenation
Breaking of a covalent bond between a substrate and a halo group.
RSC:xp
Breaking of a covalent bond between a molecule and a carboxy group.
RXNO
MOP:0001713
decarboxylation
Breaking of a covalent bond between a molecule and a carboxy group.
RSC:xp
Formation of a covalent bond between a nitrogen atom in a substrate and a methyl group.
RXNO
MOP:0002364
has_participant: CHEBI:32875
N-methylation
Formation of a covalent bond between a nitrogen atom in a substrate and a methyl group.
RSC:xp
Formation of a covalent bond between a nitrogen atom in a substrate and an alkyl group.
RXNO
MOP:0002369
has_participant: CHEBI:22323
N-alkylation
Formation of a covalent bond between a nitrogen atom in a substrate and an alkyl group.
RSC:xp
Formation of a covalent bond between a nitrogen atom in a substrate and an aryl group.
RXNO
MOP:0002411
N-arylation
Formation of a covalent bond between a nitrogen atom in a substrate and an aryl group.
RSC:xp
Formation of a covalent bond between a nitrogen atom in a substrate and an acyl group.
RXNO
MOP:0002479
has_participant: CHEBI:22221
N-acylation
Formation of a covalent bond between a nitrogen atom in a substrate and an acyl group.
RSC:xp
Formation of a covalent bond between a nitrogen atom in a substrate and a sulfonyl group.
RXNO
MOP:0002524
has_participant: CHEBI:29825
N-sulfonylation
Formation of a covalent bond between a nitrogen atom in a substrate and a sulfonyl group.
RSC:xp
Formation of a covalent bond between an oxygen atom in a substrate and a silyl group.
RXNO
MOP:0003339
has_participant: CHEBI:30541
O-silylation
Formation of a covalent bond between an oxygen atom in a substrate and a silyl group.
RSC:xp
Formation of a covalent bond between an oxygen atom in a substrate and an acyl group.
RXNO
MOP:0003479
has_participant: CHEBI:22221
O-acylation
Formation of a covalent bond between an oxygen atom in a substrate and an acyl group.
RSC:xp
Formation of a covalent bond between an oxygen atom in a substrate and a sulfonyl group.
RXNO
MOP:0003524
has_participant: CHEBI:29825
O-sulfonylation
Formation of a covalent bond between an oxygen atom in a substrate and a sulfonyl group.
RSC:xp
The formation of a covalent bond between a phosphorus atom and an alkyl group.
RXNO
MOP:0006369
P-alkylation
The formation of a covalent bond between a phosphorus atom and an alkyl group.
RSC:xp
RXNO
OBI:0000011
planned process
A reaction where the number of atoms in the molecular skeleton increases.
coupling reaction
RXNO
RXNO:0000000
molecular skeleton joining reaction
A reaction where the number of atoms in the molecular skeleton increases.
https://orcid.org/0000-0001-5985-7429
A molecular process with which the experimenters aim to achieve a particular molecular transformation.
RXNO
RXNO:0000001
planned reaction step
A molecular process with which the experimenters aim to achieve a particular molecular transformation.
https://orcid.org/0000-0001-5985-7429
A reaction where a bond is formed between two carbon atoms.
NAMERXN:3
RXNO
RXNO:0000002
carbon-carbon coupling reaction
A reaction where a bond is formed between two carbon atoms.
https://orcid.org/0000-0001-5985-7429
An aldol condensation where an aryl aldehyde reacts with an acid anhydride to form a cinnamic acid.
https://www.rsc.org/Merck-Index/reaction/r327/
https://www.wikidata.org/wiki/Q898605
RXNO
RXNO:0000003
Perkin reaction
An aldol condensation where an aryl aldehyde reacts with an acid anhydride to form a cinnamic acid.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A reaction in which the number of atoms in any ring changes between the reactant and the products.
RXNO
RXNO:0000004
This term was obsoleted because it was a grouping term that wasn't much help.
obsolete: ring reaction
true
A reaction in which the number of atoms in any ring changes between the reactant and the products.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A planned reaction step where the product contains a ring that was not in any of the reactants.
RXNO
RXNO:0000005
ring formation reaction step
A planned reaction step where the product contains a ring that was not in any of the reactants.
https://orcid.org/0000-0001-5985-7429
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.
NAMERXN:3.11.3
https://www.rsc.org/Merck-Index/reaction/r109/
https://www.wikidata.org/wiki/Q375669
Diels-Alder coupling
Diels-Alder cycloaddition
RXNO
RXNO:0000006
Diels-Alder reaction
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.
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r129/
https://www.wikidata.org/wiki/Q26469
RXNO
RXNO:0000007
ene reaction
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.
https://orcid.org/0000-0001-5985-7429
A joining reaction where a nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond).
https://www.wikidata.org/wiki/Q2181524
nucleophilic conjugate addition
RXNO
RXNO:0000008
conjugate addition
A joining reaction where a nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond).
https://orcid.org/0000-0002-4077-4719
rsc:db
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).
https://www.rsc.org/Merck-Index/reaction/r281/
https://www.wikidata.org/wiki/Q642233
Michael reaction
RXNO
RXNO:0000009
Michael addition
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).
RSC:db
A reaction where the number of atoms in the skeleton, and their connectivity, remain the same.
RXNO
RXNO:0000010
functional modification
A reaction where the number of atoms in the skeleton, and their connectivity, remain the same.
https://orcid.org/0000-0001-5985-7429
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.
NAMERXN:9
RXNO
RXNO:0000011
functional group modification
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.
rsc:db
A functional group modification reaction where a functional group is oxidised.
RXNO
RXNO:0000012
functional group oxidation
A functional group modification reaction where a functional group is oxidised.
https://orcid.org/0000-0001-5985-7429
A functional group oxidation where an aromatic amine is transformed into an aromatic diazonium salt.
diazotization
RXNO
RXNO:0000013
diazotisation
A functional group oxidation where an aromatic amine is transformed into an aromatic diazonium salt.
https://orcid.org/0000-0002-4077-4719
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.
NAMERXN:3.7
https://www.rsc.org/Merck-Index/reaction/r177/
https://www.wikidata.org/wiki/Q337748
RXNO
RXNO:0000014
Grignard reaction
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.
RSC:db
A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give an alkene.
NAMERXN:3.8
https://www.rsc.org/Merck-Index/reaction/r468/
https://www.wikidata.org/wiki/Q909735
Wittig condensation
Wittig olefination
RXNO
RXNO:0000015
Wittig reaction
A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give an alkene.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r4/
https://www.wikidata.org/wiki/Q494392
aldol reaction
RXNO
RXNO:0000016
aldol addition
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.
https://orcid.org/0000-0001-5985-7429
An aldol addition where an enol or enolate reacts with a carbonyl compound to form an alpha,beta-unsaturated ketone.
https://www.rsc.org/Merck-Index/reaction/r4/
https://www.wikidata.org/wiki/Q1027170
RXNO
RXNO:0000017
aldol condensation
An aldol addition where an enol or enolate reacts with a carbonyl compound to form an alpha,beta-unsaturated ketone.
https://orcid.org/0000-0002-4077-4719
A ring formation reaction where a 1,3-dipolar compound reacts with an alkene or alkyne to form a five-membered ring compound.
https://www.wikidata.org/wiki/Q902907
Huisgen cycloaddition
Huisgen reaction
Huisgen's 1,3-dipolar cycloaddition
RXNO
RXNO:0000018
1,3-dipolar cycloaddition
A ring formation reaction where a 1,3-dipolar compound reacts with an alkene or alkyne to form a five-membered ring compound.
RSC:db
true
true
An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide or pseudohalide to form an aromatic halide or pseudohalide.
https://www.rsc.org/Merck-Index/reaction/r386/
https://www.wikidata.org/wiki/Q898821
RXNO
RXNO:0000021
Sandmeyer reaction
An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide or pseudohalide to form an aromatic halide or pseudohalide.
RSC:db
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.
RXNO
Gattermann reaction
RXNO:0000022
This is also sometimes known as the Gattermann reaction. Also doesn't work to make fluorides or iodides.
Gattermann halogenation
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.
https://orcid.org/0000-0002-4077-4719
An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) halide to form an aromatic halide.
RXNO
RXNO:0000023
Koerner-Contardi reaction
An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) halide to form an aromatic halide.
https://orcid.org/0000-0002-4077-4719
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.
NAMERXN:3.2
https://www.rsc.org/Merck-Index/reaction/r192/
https://www.wikidata.org/wiki/Q899916
Heck-Mizoroki reaction
Mizoroki-Heck reaction
RXNO
RXNO:0000024
This usually produces the trans-olefin rather than the cis-. ALSO Merck Index gives a non-terminal example.
Heck reaction
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
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.
RXNO
RXNO:0000025
rearrangement step
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A rearrangement where an oxime rearranges to form an amide. Often there is selective migration of one group.
https://www.rsc.org/Merck-Index/reaction/r29/
https://www.wikidata.org/wiki/Q813746
RXNO
RXNO:0000026
Beckmann rearrangement
A rearrangement where an oxime rearranges to form an amide. Often there is selective migration of one group.
https://orcid.org/0000-0001-5985-7429
true
A [3,3]-sigmatropic rearrangement where a 1,5-hexadiene rearranges to form a 1,5-hexadiene.
https://www.rsc.org/Merck-Index/reaction/r86/
https://www.wikidata.org/wiki/Q905087
RXNO
RXNO:0000028
Cope rearrangement
A [3,3]-sigmatropic rearrangement where a 1,5-hexadiene rearranges to form a 1,5-hexadiene.
https://orcid.org/0000-0001-5985-7429
A [3,3]-sigmatropic rearrangement of a 3-hydroxy-1,5-hexadiene rearranges to form a 5,6-unsaturated carbonyl compound.
https://www.rsc.org/Merck-Index/reaction/r86/
https://www.wikidata.org/wiki/Q25326942
RXNO
RXNO:0000029
oxy-Cope rearrangement
A [3,3]-sigmatropic rearrangement of a 3-hydroxy-1,5-hexadiene rearranges to form a 5,6-unsaturated carbonyl compound.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A joining reaction in which one or more atoms are added to the middle of a chain.
RXNO
RXNO:0000030
molecular skeleton insertion reaction
A joining reaction in which one or more atoms are added to the middle of a chain.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
RXNO:0000190
https://www.rsc.org/Merck-Index/reaction/r13/
https://www.wikidata.org/wiki/Q182033
B-V reaction
Baeyer-Villiger oxidative rearrangement
Baeyer-Villiger reaction
RXNO
Baeyer-Villiger rearrangement
RXNO:0000031
Baeyer-Villiger oxidation
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.
https://orcid.org/0000-0002-4077-4719
rsc:db
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.
https://www.rsc.org/Merck-Index/reaction/r265/
https://www.wikidata.org/wiki/Q183055
RXNO
RXNO:0000032
Mannich reaction
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.
RSC:db
true
A substitution where an alcohol is converted into something else. Typical reagents are a dialkyl azodicarboxylate and a triarylphosphine. The alcohol stereocentre is inverted.
https://www.rsc.org/Merck-Index/reaction/r287/
https://www.wikidata.org/wiki/Q899062
RXNO
RXNO:0000034
Mitsunobu reaction
A substitution where an alcohol is converted into something else. Typical reagents are a dialkyl azodicarboxylate and a triarylphosphine. The alcohol stereocentre is inverted.
RSC:db
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction where a stannane reacts with an organohalide or organotriflate.
NAMERXN:3.4
https://www.rsc.org/Merck-Index/reaction/r415/
https://www.wikidata.org/wiki/Q899861
Stille reaction
RXNO
RXNO:0000035
Stille coupling
A carbon-carbon coupling reaction where a stannane reacts with an organohalide or organotriflate.
RSC:db
A carbon-carbon coupling reaction where an aldehyde or amine reacts with a alpha-halo ester and zinc to form a beta-hydroxy ester.
https://www.rsc.org/Merck-Index/reaction/r361/
https://www.wikidata.org/wiki/Q898948
Reformatskii reaction
RXNO
RXNO:0000036
Reformatsky reaction
A carbon-carbon coupling reaction where an aldehyde or amine reacts with a alpha-halo ester and zinc to form a beta-hydroxy ester.
https://orcid.org/0000-0001-5985-7429
A functional group modification reaction where a functional group is reduced.
RXNO
RXNO:0000037
functional group reduction
A functional group modification reaction where a functional group is reduced.
https://orcid.org/0000-0001-5985-7429
A functional group reduction where an aldehyde or ketone carbonyl group is reduced to a methylene with zinc-mercury amalgam and hydrochloric acid.
https://www.rsc.org/Merck-Index/reaction/r82/
https://www.wikidata.org/wiki/Q898480
RXNO
RXNO:0000038
Clemmensen reduction
A functional group reduction where an aldehyde or ketone carbonyl group is reduced to a methylene with zinc-mercury amalgam and hydrochloric acid.
RSC:db
A joining reaction where a carbon-carbon bond is formed between like moieties.
RXNO
RXNO:0000039
carbon-carbon homocoupling reaction
A joining reaction where a carbon-carbon bond is formed between like moieties.
https://orcid.org/0000-0001-5985-7429
A carbon-carbon homocoupling reaction of an aryl halide mediated by copper.
https://www.rsc.org/Merck-Index/reaction/r441/
https://www.wikidata.org/wiki/Q904703
RXNO
RXNO:0000040
Ullmann reaction
A carbon-carbon homocoupling reaction of an aryl halide mediated by copper.
https://orcid.org/0000-0001-5985-7429
A reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order.
RXNO
RXNO:0000041
addition reaction step
A reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order.
https://orcid.org/0000-0001-5985-7429
Addition of hydrogen atoms to aromatic rings by means of alkali metals in liquid ammonia.
https://www.rsc.org/Merck-Index/reaction/r44/
https://www.wikidata.org/wiki/Q864996
RXNO
RXNO:0000042
Birch reduction
Addition of hydrogen atoms to aromatic rings by means of alkali metals in liquid ammonia.
https://orcid.org/0000-0001-5985-7429
A carbon-carbon coupling reaction of an ester and a carbonyl compound to form a beta-keto ester.
https://www.rsc.org/Merck-Index/reaction/r79/
https://www.wikidata.org/wiki/Q898501
RXNO
RXNO:0000043
Claisen condensation
A carbon-carbon coupling reaction of an ester and a carbonyl compound to form a beta-keto ester.
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction of an aldehyde and a methylene compound.
https://www.rsc.org/Merck-Index/reaction/r230/
https://www.wikidata.org/wiki/Q898972
RXNO
RXNO:0000044
Knoevenagel condensation
A carbon-carbon coupling reaction of an aldehyde and a methylene compound.
https://orcid.org/0000-0001-5985-7429
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.
https://www.rsc.org/Merck-Index/reaction/r158/
https://www.wikidata.org/wiki/Q15130933
RXNO
RXNO:0000045
Friedel-Crafts acylation
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r158/
RXNO
RXNO:0000046
It proceeds by an SN1 mechanism.
Friedel-Crafts alkylation
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r311/
https://www.wikidata.org/wiki/Q902263
RXNO
RXNO:0000047
Oppenauer oxidation
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling between formaldehyde and an alkene to give a 1,3-diol or an allylic alcohol, catalysed by acid.
https://www.rsc.org/Merck-Index/reaction/r352/
https://www.wikidata.org/wiki/Q267374
RXNO
RXNO:0000048
See also "intramolecular Prins reaction".
Prins reaction
A carbon-carbon coupling between formaldehyde and an alkene to give a 1,3-diol or an allylic alcohol, catalysed by acid.
RSC:db
https://orcid.org/0000-0002-4077-4719
A reaction between formaldehyde and an alkene to give a 1,3-dioxane, catalysed by acid.
https://www.rsc.org/Merck-Index/reaction/r352/
RXNO
RXNO:0000049
intramolecular Prins reaction
A reaction between formaldehyde and an alkene to give a 1,3-dioxane, catalysed by acid.
RSC:db
https://orcid.org/0000-0002-4077-4719
A rearrangement of a 1,2-diol to give a carbonyl compound, catalysed by acid.
https://www.rsc.org/Merck-Index/reaction/r341/
https://www.wikidata.org/wiki/Q902209
RXNO
RXNO:0000050
pinacol rearrangement
A rearrangement of a 1,2-diol to give a carbonyl compound, catalysed by acid.
RSC:db
https://orcid.org/0000-0002-4077-4719
A rearrangement of a diazoketone to give a ketene, with the elimination of molecular nitrogen.
https://www.rsc.org/Merck-Index/reaction/r474/
https://www.wikidata.org/wiki/Q255452
RXNO
RXNO:0000051
Wolff rearrangement
A rearrangement of a diazoketone to give a ketene, with the elimination of molecular nitrogen.
RSC:db
https://orcid.org/0000-0002-4077-4719
A reaction in which a fused ring system is present in a product that was not present in any of the reactants.
RXNO
RXNO:0000052
fused-ring-system formation
A reaction in which a fused ring system is present in a product that was not present in any of the reactants.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A cyclodehydration of a beta-phenethylamide to give a 3,4-dihydroisoquinoline.
https://www.rsc.org/Merck-Index/reaction/r46/
https://www.wikidata.org/wiki/Q866098
Bischler-Napieralski 3,4-dihydroisoquinoline synthesis
Bischler-Napieralski dihydroisoquinoline synthesis
Bischler-Napieralski isoquinoline synthesis
RXNO
RXNO:0000053
Bischler-Napieralski reaction
A cyclodehydration of a beta-phenethylamide to give a 3,4-dihydroisoquinoline.
RSC:db
https://orcid.org/0000-0002-4077-4719
A rearrangement of an acyl azide to give an isocyanate by pyrolysis, with the elimination of molecular nitrogen.
https://www.rsc.org/Merck-Index/reaction/r97/
https://www.wikidata.org/wiki/Q254370
Curtius degradation
Curtius reaction
RXNO
RXNO:0000054
Curtius rearrangement
A rearrangement of an acyl azide to give an isocyanate by pyrolysis, with the elimination of molecular nitrogen.
RSC:db
https://orcid.org/0000-0002-4077-4719
A formylation of an activated arene with a disubstituted formamide to give an arenecarbaldehyde.
https://www.rsc.org/Merck-Index/reaction/r444/
https://www.wikidata.org/wiki/Q903038
Vilsmeier-Haack formylation
RXNO
RXNO:0000055
Vilsmeier-Haack reaction
A formylation of an activated arene with a disubstituted formamide to give an arenecarbaldehyde.
RSC:db
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction between a phosphonate and a carbonyl compound to give an olefin.
https://www.rsc.org/Merck-Index/reaction/r468/
https://www.wikidata.org/wiki/Q905020
Emmons reaction
Horner-Emmons reaction
Horner-Emmons-Wadsworth reaction
Horner-Wadsworth-Emmons (HWE) olefination
Horner-Wadsworth-Emmons olefination
Horner-Wittig reaction
Wadsworth-Emmons olefination
Wadsworth-Emmons reaction
Wadsworth-Emmons-Horner reaction
Wittig-Horner reaction
RXNO
RXNO:0000056
Horner-Wadsworth-Emmons reaction
A carbon-carbon coupling reaction between a phosphonate and a carbonyl compound to give an olefin.
RSC:db
https://orcid.org/0000-0002-4077-4719
A joining reaction between a phosphine oxide and a carbonyl compound to give an olefin.
https://www.rsc.org/Merck-Index/reaction/r468/
RXNO
RXNO:0000057
Horner reaction
A joining reaction between a phosphine oxide and a carbonyl compound to give an olefin.
RSC:db
https://orcid.org/0000-0002-4077-4719
A reaction between an alcohol or alkene and a nitrile to give an amide, catalysed by a Bronsted acid.
https://www.rsc.org/Merck-Index/reaction/r372/
https://www.wikidata.org/wiki/Q902273
RXNO
RXNO:0000058
Proceeds by an SN1 mechanism.
Ritter reaction
A reaction between an alcohol or alkene and a nitrile to give an amide, catalysed by a Bronsted acid.
RSC:db
https://orcid.org/0000-0002-4077-4719
A condensation-cyclisation of a beta-phenethylamine with an aldehyde to give a tetrahydroisoquinoline.
https://www.rsc.org/Merck-Index/reaction/r338/
https://www.wikidata.org/wiki/Q899206
Pictet-Spengler isoquinoline synthesis
Pictet-Spengler tetrahydroisoquinoline synthesis
RXNO
RXNO:0000059
Pictet-Spengler reaction
A condensation-cyclisation of a beta-phenethylamine with an aldehyde to give a tetrahydroisoquinoline.
RSC:db
https://orcid.org/0000-0002-4077-4719
The alkylation of a trialkyl phosphite with an alkyl halide or acyl halide to give an alkyl phosphonate.
RXNO:0000112
https://www.wikidata.org/wiki/Q630801
Michaelis-Arbuzov phosphonate synthesis
Michaelis-Arbuzov reaction
RXNO
RXNO:0000060
Arbuzov reaction
The alkylation of a trialkyl phosphite with an alkyl halide or acyl halide to give an alkyl phosphonate.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.wikidata.org/wiki/Q1059787
Mukaiyama aldol addition
Mukaiyama aldol reaction
RXNO
RXNO:0000061
Mukaiyama aldol condensation
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
A condensation between an aromatic amine and glycerol to give a quinoline.
https://www.rsc.org/Merck-Index/reaction/r403/
https://www.wikidata.org/wiki/Q903836
Skraup quinoline synthesis
RXNO
RXNO:0000062
Skraup reaction
A condensation between an aromatic amine and glycerol to give a quinoline.
RSC:db
https://orcid.org/0000-0002-4077-4719
A homologation reaction of a carboxylic acid to give the homologated carboxylic acid via acyl chloride and diazoketone intermediates.
https://www.rsc.org/Merck-Index/reaction/r10/
https://www.wikidata.org/wiki/Q137617
Arndt-Eistert synthesis
RXNO
RXNO:0000063
This is an insertion because the carbon atom is added between the R group and the carboxyl carbon in the starting material.
Arndt-Eistert reaction
A homologation reaction of a carboxylic acid to give the homologated carboxylic acid via acyl chloride and diazoketone intermediates.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
Reaction of an aldehyde or ketone with a phenylhydrazine to give an indole.
https://www.wikidata.org/wiki/Q901218
Fischer indolisation
Fischer indolization
RXNO
RXNO:0000064
Fischer indole synthesis
Reaction of an aldehyde or ketone with a phenylhydrazine to give an indole.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
An intramolecular cyclisation of a diester to give a cyclic beta-ketoester.
https://www.rsc.org/Merck-Index/reaction/r108/
https://www.wikidata.org/wiki/Q900932
Dieckmann condensation
Dieckmann cyclization
Dieckmann reaction
RXNO
RXNO:0000065
This is the intramolecular version of the Claisen condensation.
Dieckmann cyclisation
An intramolecular cyclisation of a diester to give a cyclic beta-ketoester.
RSC:db
https://orcid.org/0000-0002-4077-4719
A joining of an organic azide and a tertiary phosphine to give a phosphazo compound.
https://www.wikidata.org/wiki/Q903726
Staudinger ligation
Staudinger reduction
RXNO
RXNO:0000066
Hydrolysis of the phosphazo compound gives the corresponding amine." [https://orcid.org/0000-0002-4077-4719, RSC:db]
Staudinger reaction
A joining of an organic azide and a tertiary phosphine to give a phosphazo compound.
RSC:db
https://orcid.org/0000-0002-4077-4719
A rearrangement of a hydrazobenzene to give a diaminobiphenyl compound.
https://www.rsc.org/Merck-Index/reaction/r33/
https://www.wikidata.org/wiki/Q465781
RXNO
RXNO:0000067
benzidine rearrangement
A rearrangement of a hydrazobenzene to give a diaminobiphenyl compound.
RSC:db
https://orcid.org/0000-0002-4077-4719
A rearrangement of a p-substituted hydrazobenzene to give a p-aminodiphenylamine.
https://www.rsc.org/Merck-Index/reaction/r33/
RXNO
RXNO:0000068
semidine rearrangement
A rearrangement of a p-substituted hydrazobenzene to give a p-aminodiphenylamine.
RSC:db
https://orcid.org/0000-0002-4077-4719
A rearrangement of a heterocyclic compound in which endocyclic and exocyclic heteroatoms swap places.
https://www.rsc.org/Merck-Index/reaction/r111/
https://www.wikidata.org/wiki/Q902659
RXNO
RXNO:0000069
Dimroth rearrangement
A rearrangement of a heterocyclic compound in which endocyclic and exocyclic heteroatoms swap places.
RSC:db
https://orcid.org/0000-0002-4077-4719
A molecular skeleton joining reaction in which a chain part of a molecular skeleton is lengthened.
RXNO
RXNO:0000070
chain lengthening
A molecular skeleton joining reaction in which a chain part of a molecular skeleton is lengthened.
https://orcid.org/0000-0001-5985-7429
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.
https://www.rsc.org/Merck-Index/reaction/r122/
https://www.wikidata.org/wiki/Q898506
RXNO
RXNO:0000071
The latter can be used to identify the terminal amino acid, and the process repeated to enable peptide sequencing."
Edman degradation
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
A formylation reaction between a phenol and chloroform (for example, to form an ortho-formyl phenol).
https://www.rsc.org/Merck-Index/reaction/r362/
RXNO
RXNO:0000072
Reimer-Tiemann reaction
A formylation reaction between a phenol and chloroform (for example, to form an ortho-formyl phenol).
RSC:db
https://orcid.org/0000-0002-4077-4719
A reaction where atoms are lost from the molecular skeleton.
RXNO
RXNO:0000073
cleaving reaction
A reaction where atoms are lost from the molecular skeleton.
https://orcid.org/0000-0001-5985-7429
A carbon-carbon homocoupling reaction of two molecules of an alkyl halide with sodium to give a symmetrical product.
https://www.rsc.org/Merck-Index/reaction/r478/
https://www.wikidata.org/wiki/Q898901
Wurtz coupling
RXNO
RXNO:0000074
Wurtz reaction
A carbon-carbon homocoupling reaction of two molecules of an alkyl halide with sodium to give a symmetrical product.
RSC:db
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r34/
https://www.wikidata.org/wiki/Q818488
RXNO
RXNO:0000075
benzilic acid rearrangement
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling of an aldehyde to an activated alkene in the presence of a nucleophilic base to give an alpha-hydroxyalkylated compound.
https://www.rsc.org/Merck-Index/reaction/r27/
https://www.wikidata.org/wiki/Q812563
MBH reaction
Morita-Baylis-Hillman reaction
RXNO
RXNO:0000076
Baylis-Hillman reaction
A carbon-carbon coupling of an aldehyde to an activated alkene in the presence of a nucleophilic base to give an alpha-hydroxyalkylated compound.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r101/
https://www.wikidata.org/wiki/Q899351
Darzens condensation
Darzens-Claisen reaction
glycidic ester condensation
RXNO
RXNO:0000077
Darzens reaction
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
A reaction in which a functional group is modified by converting it into a protecting group, in order to make subsequent reactions more selective.
NAMERXN:5
RXNO
RXNO:0000078
protection reaction
A reaction in which a functional group is modified by converting it into a protecting group, in order to make subsequent reactions more selective.
https://orcid.org/0000-0001-5985-7429
A protection reaction in which an amine is converted into a tert-butoxycarbonyl compound.
RXNO
RXNO:0000079
Boc protection
A protection reaction in which an amine is converted into a tert-butoxycarbonyl compound.
RSC:db
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r331/
https://www.wikidata.org/wiki/Q900350
Peterson reaction
RXNO
RXNO:0000080
Peterson olefination
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
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.
https://www.wikidata.org/wiki/Q2371705
Ullmann ether synthesis
RXNO
RXNO:0000081
Ullmann condensation
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
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.
RXNO
RXNO:0000082
Goldberg reaction
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
A photochemical cycloaddition between an aldehyde or ketone and an alkene to give an oxetane.
https://www.rsc.org/Merck-Index/reaction/r319/
https://www.wikidata.org/wiki/Q902254
Paterno-Buchi reaction
RXNO
RXNO:0000083
Paternò–Büchi reaction
A photochemical cycloaddition between an aldehyde or ketone and an alkene to give an oxetane.
RSC:db
https://orcid.org/0000-0002-4077-4719
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.
https://www.wikidata.org/wiki/Q807848
RXNO
RXNO:0000084
Barbier reaction
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
A reductive coupling reaction between two esters to give an acyloin (an alpha-hydroxyketone).
https://www.rsc.org/Merck-Index/reaction/r2/
https://www.wikidata.org/wiki/Q345007
RXNO
RXNO:0000085
acyloin condensation
A reductive coupling reaction between two esters to give an acyloin (an alpha-hydroxyketone).
RSC:db
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction between a nitroalkane and an aldehyde or ketone to give a beta-hydroxy nitroalkane.
https://www.rsc.org/Merck-Index/reaction/r196/
https://www.wikidata.org/wiki/Q903747
nitro-aldol reaction
nitroaldol reaction
RXNO
RXNO:0000086
Henry reaction
A carbon-carbon coupling reaction between a nitroalkane and an aldehyde or ketone to give a beta-hydroxy nitroalkane.
RSC:db
https://orcid.org/0000-0002-4077-4719
The photolytic oxidation of a nitrate ester to give a gamma-nitroalcohol.
https://www.rsc.org/Merck-Index/reaction/r24/
https://www.wikidata.org/wiki/Q809549
RXNO
RXNO:0000087
Barton reaction
The photolytic oxidation of a nitrate ester to give a gamma-nitroalcohol.
RSC:db
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction between an organohalide or organotriflate and an organozinc compound. The reaction is catalysed by palladium or nickel.
https://www.rsc.org/Merck-Index/reaction/r299/
https://www.wikidata.org/wiki/Q902756
Negishi cross-coupling
RXNO
RXNO:0000088
Negishi coupling
A carbon-carbon coupling reaction between an organohalide or organotriflate and an organozinc compound. The reaction is catalysed by palladium or nickel.
RSC:db
https://orcid.org/0000-0002-4077-4719
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).
https://www.rsc.org/Merck-Index/reaction/r272/
https://www.wikidata.org/wiki/Q903026
RXNO
RXNO:0000089
Meerwein-Ponndorf-Verley reduction
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).
RSC:db
https://orcid.org/0000-0002-4077-4719
The reaction between an alkyl halide or alkyl sulfate and a metal alkoxide to give an ether.
https://www.wikidata.org/wiki/Q898790
Williamson etherification
RXNO
RXNO:0000090
Williamson ether synthesis
The reaction between an alkyl halide or alkyl sulfate and a metal alkoxide to give an ether.
RSC:db
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give a terminal alkene.
RXNO
RXNO:0000091
Wittig methylenation
A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give a terminal alkene.
https://orcid.org/0000-0001-5985-7429
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.
https://www.wikidata.org/wiki/Q2042393
aza Diels-Alder cycloaddition
aza Diels-Alder reaction
aza-Diels-Alder cycloaddition
azo Diels-Alder cycloaddition
azo Diels-Alder reaction
azo-Diels-Alder cycloaddition
azo-Diels-Alder reaction
RXNO
RXNO:0000092
aza-Diels-Alder reaction
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
A cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule.
https://www.wikidata.org/wiki/Q31287730
RXNO
RXNO:0000093
extrusion reaction
A cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule.
https://orcid.org/0000-0001-5985-7429
The reaction of an alpha-halosulfone to give an alkene, with the extrusion of sulfur dioxide.
https://www.wikidata.org/wiki/Q1935557
Ramberg-Backlund reaction
RXNO
RXNO:0000094
Ramberg-Bäcklund reaction
The reaction of an alpha-halosulfone to give an alkene, with the extrusion of sulfur dioxide.
RSC:db
https://orcid.org/0000-0002-4077-4719
The rearrangement of an aromatic nitrosamine to a para-nitrosoaniline.
https://www.wikidata.org/wiki/Q1968891
RXNO
RXNO:0000095
Fischer-Hepp rearrangement
The rearrangement of an aromatic nitrosamine to a para-nitrosoaniline.
RSC:db
https://orcid.org/0000-0002-4077-4719
A coupling reaction of a diazonium salt with a phenol or aniline to give an azo compound.
https://www.wikidata.org/wiki/Q668665
RXNO
RXNO:0000096
azo coupling
A coupling reaction of a diazonium salt with a phenol or aniline to give an azo compound.
RSC:db
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction where an imine reacts with a alpha-halo ester and zinc to form a beta-amino ester.
imino Reformatsky reaction
RXNO
RXNO:0000097
imino-Reformatsky reaction
A carbon-carbon coupling reaction where an imine reacts with a alpha-halo ester and zinc to form a beta-amino ester.
https://orcid.org/0000-0001-5985-7429
A coupling reaction between two molecules of a terminal alkyne catalysed by Cu(I) salts.
https://www.rsc.org/Merck-Index/reaction/r169/
https://www.wikidata.org/wiki/Q514335
RXNO
RXNO:0000098
Glaser coupling
A coupling reaction between two molecules of a terminal alkyne catalysed by Cu(I) salts.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A coupling reaction between two molecules of a terminal alkyne using stoichiometric Cu(II) salts.
https://www.rsc.org/Merck-Index/reaction/r169/
Eglinton coupling
RXNO
RXNO:0000099
Eglinton reaction
A coupling reaction between two molecules of a terminal alkyne using stoichiometric Cu(II) salts.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A coupling reaction between a terminal alkyne and an alkynyl halide catalysed by Cu(I) salts.
https://www.rsc.org/Merck-Index/reaction/r169/
https://www.wikidata.org/wiki/Q903015
RXNO
RXNO:0000100
Cadiot-Chodkiewicz coupling
A coupling reaction between a terminal alkyne and an alkynyl halide catalysed by Cu(I) salts.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reductive amination of ketones or aldehydes with an ammonium formate or formamide to form an amine.
https://www.wikidata.org/wiki/Q726513
RXNO
RXNO:0000101
Leuckart reaction
The reductive amination of ketones or aldehydes with an ammonium formate or formamide to form an amine.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reductive amination of ketones or aldehydes with an amine and formic acid to form amines.
https://www.wikidata.org/wiki/Q726513
Wallach reaction
RXNO
RXNO:0000102
Leuckart-Wallach reaction
The reductive amination of ketones or aldehydes with an amine and formic acid to form amines.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by hydrolysis, to give the corresponding primary amine.
https://www.wikidata.org/wiki/Q123422
RXNO
RXNO:0000103
Gabriel synthesis
The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by hydrolysis, to give the corresponding primary amine.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by treatment with hydrazine, to give the corresponding primary amine.
RXNO
RXNO:0000104
Ing-Manske procedure
The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by treatment with hydrazine, to give the corresponding primary amine.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A reaction in which a single skeletal atom is removed from the end of a chain.
RXNO
RXNO:0000105
end-of-chain chain shortening
A reaction in which a single skeletal atom is removed from the end of a chain.
https://orcid.org/0000-0001-5985-7429
The decarboxylation of silver carboxylates with halogens to give organic halides.
https://www.rsc.org/Merck-Index/reaction/r215/
https://www.wikidata.org/wiki/Q902216
Borodin reaction
Borodine reaction
RXNO
RXNO:0000106
Hunsdiecker reaction
The decarboxylation of silver carboxylates with halogens to give organic halides.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r264/
https://www.wikidata.org/wiki/Q902284
RXNO
RXNO:0000107
malonic ester synthesis
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A reaction in which an existing ring is increased in size.
ring enlargement
RXNO
RXNO:0000108
ring expansion
A reaction in which an existing ring is increased in size.
https://orcid.org/0000-0001-5985-7429
The reaction between isatin and an alpha-methylene carbonyl compound to give a substituted quinoline-4-carboxylic acid.
https://www.rsc.org/Merck-Index/reaction/r334/
https://www.wikidata.org/wiki/Q1580484
Pfitzinger quinoline synthesis
Pfitzinger-Borsche reaction
RXNO
RXNO:0000109
Pfitzinger reaction
The reaction between isatin and an alpha-methylene carbonyl compound to give a substituted quinoline-4-carboxylic acid.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A reaction in which the parent molecule breaks up into three or more products.
RXNO
RXNO:0000110
fragmentation reaction
A reaction in which the parent molecule breaks up into three or more products.
https://orcid.org/0000-0001-5985-7429
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.
https://www.wikidata.org/wiki/Q5609896
RXNO
RXNO:0000111
Grob fragmentation
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
true
The rearrangement of an alpha-, beta- or gamma-hydroxy silane to give a silyl ether. It is catalysed by a base.
https://www.rsc.org/Merck-Index/reaction/r62/
https://www.wikidata.org/wiki/Q2558021
RXNO
RXNO:0000113
Brook rearrangement
The rearrangement of an alpha-, beta- or gamma-hydroxy silane to give a silyl ether. It is catalysed by a base.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophile to give a substituted alkyne.
https://www.rsc.org/Merck-Index/reaction/r303/
https://www.wikidata.org/wiki/Q902932
RXNO
RXNO:0000114
Nicholas reaction
The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophile to give a substituted alkyne.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a hydride or amine or enamine to give a substituted alkyne.
RXNO
RXNO:0000115
Nicholas reaction, nucleophilic heteroatom centre
The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a hydride or amine or enamine to give a substituted alkyne.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
RXNO
RXNO:0000116
Nicholas reaction, nucleophilic carbon centre
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction between a phenyl sulfone and an aldehyde or ketone to give a (typically trans) alkene.
https://www.rsc.org/Merck-Index/reaction/r224/
https://www.wikidata.org/wiki/Q902237
Julia-Lythgoe olefination
RXNO
RXNO:0000117
Julia olefination
A carbon-carbon coupling reaction between a phenyl sulfone and an aldehyde or ketone to give a (typically trans) alkene.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The oxidation of a benzylic halide to give an aldehyde. The reaction uses hexamethylenetetramine.
https://www.wikidata.org/wiki/Q909040
RXNO
RXNO:0000118
Sommelet reaction
The oxidation of a benzylic halide to give an aldehyde. The reaction uses hexamethylenetetramine.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reduction of an ester using sodium to give two alcohols.
https://www.rsc.org/Merck-Index/reaction/r58/
https://www.wikidata.org/wiki/Q895315
Bouveault-Blanc procedure
Bouveault-Blanc reduction
RXNO
RXNO:0000119
Bouveault-Blanc reaction
The reduction of an ester using sodium to give two alcohols.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A base-catalysed isomerisation of a 2,3-epoxyalcohol, with inversion of configuration at C2.
https://www.rsc.org/Merck-Index/reaction/r321/
https://www.wikidata.org/wiki/Q983127
RXNO
RXNO:0000120
Payne rearrangement
A base-catalysed isomerisation of a 2,3-epoxyalcohol, with inversion of configuration at C2.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A base-catalysed isomerisation of a 2,3-epoxyamine to form a hydroxy aziridine, with inversion of configuration at C2.
https://www.rsc.org/Merck-Index/reaction/r321/
RXNO
RXNO:0000121
aza-Payne rearrangement
A base-catalysed isomerisation of a 2,3-epoxyamine to form a hydroxy aziridine, with inversion of configuration at C2.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The base-catalysed rearrangement of an o-acetoxyacetophenone to give a hydroxyphenyl-1,3-diketone.
https://www.rsc.org/Merck-Index/reaction/r14/
https://www.wikidata.org/wiki/Q804325
RXNO
RXNO:0000122
Baker-Venkataraman rearrangement
The base-catalysed rearrangement of an o-acetoxyacetophenone to give a hydroxyphenyl-1,3-diketone.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order.
RXNO
RXNO:0000123
This is narrower in focus than elimination in general in that we're focussing on the aims of the chemist.
molecular skeleton elimination reaction
A reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order.
https://orcid.org/0000-0001-5985-7429
The reaction of a tosylhydrazone of an aldehyde or ketone with a strong base to give an olefin.
https://www.rsc.org/Merck-Index/reaction/r16/
https://www.wikidata.org/wiki/Q575939
RXNO
RXNO:0000124
This generally provides the more-substituted olefin as the thermodynamic product.
Bamford-Stevens reaction
The reaction of a tosylhydrazone of an aldehyde or ketone with a strong base to give an olefin.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reaction of a tosylhydrazone of an aldehyde or ketone with an alkyllithium or Grignard reagent to give an olefin.
https://www.rsc.org/Merck-Index/reaction/r16/
https://www.wikidata.org/wiki/Q846597
RXNO
RXNO:0000125
This generally provides the less-substituted olefin as the kinetic product.
Shapiro reaction
The reaction of a tosylhydrazone of an aldehyde or ketone with an alkyllithium or Grignard reagent to give an olefin.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reaction between an aromatic amine, an aldehyde and pyruvic acid on heating to give a quinoline 4-carboxylic acid (cinchoninic acid).
https://www.rsc.org/Merck-Index/reaction/r114/
https://www.wikidata.org/wiki/Q3772250
RXNO
RXNO:0000126
Doebner reaction
The reaction between an aromatic amine, an aldehyde and pyruvic acid on heating to give a quinoline 4-carboxylic acid (cinchoninic acid).
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The conversion of an aromatic amine to the corresponding fluoride via the diazonium fluoroborate.
https://www.rsc.org/Merck-Index/reaction/r388/
https://www.wikidata.org/wiki/Q572113
Schiemann reaction
RXNO
RXNO:0000127
Balz-Schiemann reaction
The conversion of an aromatic amine to the corresponding fluoride via the diazonium fluoroborate.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The decarboxylation and coupling of a carboxylate or mixture of carboxylates to give a dimer.
https://www.rsc.org/Merck-Index/reaction/r238/
https://www.wikidata.org/wiki/Q901771
Crum-Brown-Walker reaction
Kolbe electrolytic synthesis
Kolbe electrosynthesis
Kolbe reaction
RXNO
RXNO:0000128
Kolbe electrolysis
The decarboxylation and coupling of a carboxylate or mixture of carboxylates to give a dimer.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
Reaction of a ketone or aldehyde, amine, an isocyanide and carboxylic acid to form a bisamide.
https://www.rsc.org/Merck-Index/reaction/r440/
https://www.wikidata.org/wiki/Q2002373
4CC
Ugi four-component condensation
Ugi-4CR
RXNO
RXNO:0000129
Ugi reaction
Reaction of a ketone or aldehyde, amine, an isocyanide and carboxylic acid to form a bisamide.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r452/
Wacker oxidation
Wacker reaction
RXNO
RXNO:0000130
Wacker-Tsuji oxidation
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The oxidation of ethene to acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant.
https://www.wikidata.org/wiki/Q578923
RXNO
RXNO:0000131
Wacker process
The oxidation of ethene to acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reaction of carbon monoxide with methanol to form acetic acid, catalysed by a rhodium complex.
https://www.wikidata.org/wiki/Q901246
RXNO
RXNO:0000132
Monsanto process
The reaction of carbon monoxide with methanol to form acetic acid, catalysed by a rhodium complex.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reaction of carbon monoxide with methanol to form acetic acid, catalysed by an iridium complex.
https://www.wikidata.org/wiki/Q579304
RXNO
RXNO:0000133
Cativa process
The reaction of carbon monoxide with methanol to form acetic acid, catalysed by an iridium complex.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The deoxygenation of an alcohol to the corresponding alkane using a thiochloroformate. It proceeds by a radical mechanism.
https://www.rsc.org/Merck-Index/reaction/r22/
https://www.wikidata.org/wiki/Q809548
Barton deoxygenation
Barton reduction
RXNO
RXNO:0000134
Barton-McCombie deoxygenation
The deoxygenation of an alcohol to the corresponding alkane using a thiochloroformate. It proceeds by a radical mechanism.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The decarboxylation of a carboxylic acid to the lower homologue alkane using a pyridine thione.
https://www.rsc.org/Merck-Index/reaction/r21/
https://www.wikidata.org/wiki/Q3454335
RXNO
RXNO:0000135
The reaction proceeds by a radical mechanism.
Barton decarboxylation
The decarboxylation of a carboxylic acid to the lower homologue alkane using a pyridine thione.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The hydrogenolysis of an acyl halide to the corresponding aldehyde, catalysed by palladium-on-barium sulfate.
https://www.rsc.org/Merck-Index/reaction/r375/
https://www.wikidata.org/wiki/Q905524
Rosenmund reaction
RXNO
RXNO:0000136
Rosenmund reduction
The hydrogenolysis of an acyl halide to the corresponding aldehyde, catalysed by palladium-on-barium sulfate.
https://orcid.org/0000-0002-4077-4719
rsc:db
A carbon-carbon coupling reaction where a terminal alkyne reacts with an aryl halide to give an aryl alkyne. It is catalysed by palladium.
NAMERXN:3.3
https://www.rsc.org/Merck-Index/reaction/r408/
https://www.wikidata.org/wiki/Q900334
Hagihara-Sonogashira coupling
Sonogashira cross-coupling
Sonogashira reaction
RXNO
RXNO:0000137
Sonogashira coupling
A carbon-carbon coupling reaction where a terminal alkyne reacts with an aryl halide to give an aryl alkyne. It is catalysed by palladium.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A reaction between two aromatic aldehydes to give a benzoin (an alpha-hydroxyketone).
https://www.rsc.org/Merck-Index/reaction/r35/
https://www.wikidata.org/wiki/Q818514
benzoin addition
RXNO
RXNO:0000138
benzoin condensation
A reaction between two aromatic aldehydes to give a benzoin (an alpha-hydroxyketone).
RSC:db
https://orcid.org/0000-0002-4077-4719
The formylation of an arene with hydrogen cyanide to give an aryl aldehyde or ketone.
RXNO
RXNO:0000139
This is essentially a variant of the Friedel-Crafts acylation.
Gattermann reaction
The formylation of an arene with hydrogen cyanide to give an aryl aldehyde or ketone.
RSC:db
https://orcid.org/0000-0002-4077-4719
The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate catalysed by a palladium(0) complex.
NAMERXN:3.1
https://www.rsc.org/Merck-Index/reaction/r424/
https://www.wikidata.org/wiki/Q899891
Suzuki coupling reaction
Suzuki cross-coupling
Suzuki cross-coupling reaction
Suzuki reaction
Suzuki-Miyaura coupling
Suzuki-Miyaura coupling reaction
Suzuki-Miyaura cross-coupling
Suzuki-Miyaura cross-coupling reaction
Suzuki-Miyaura reaction
RXNO
RXNO:0000140
Suzuki-Miyaura coupling
The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate catalysed by a palladium(0) complex.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r397/
https://www.wikidata.org/wiki/Q56672072
Katsuki-Sharpless asymmetric epoxidation
Katsuki-Sharpless epoxidation
Sharpless epoxidation
Sharpless-Katsuki asymmetric epoxidation
Sharpless-Katsuki epoxidation
RXNO
RXNO:0000141
Sharpless asymmetric epoxidation
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r396/
https://www.wikidata.org/wiki/Q752651
Sharpless bishydroxylation
Sharpless hydroxylation
RXNO
RXNO:0000142
Sharpless asymmetric dihydroxylation
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
Sharpless oxyamination
RXNO
RXNO:0000143
Sharpless asymmetric aminohydroxylation
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r248/
https://www.wikidata.org/wiki/Q899278
Kharasch cross-coupling
Kumada cross-coupling
RXNO
RXNO:0000144
Kumada coupling
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The degradation of a carboxylic acid to its next lower homologous carboxylic acid.
https://www.rsc.org/Merck-Index/reaction/r18/
https://www.wikidata.org/wiki/Q5801440
Barbier-Wieland procedure
RXNO
RXNO:0000145
Barbier-Wieland degradation
The degradation of a carboxylic acid to its next lower homologous carboxylic acid.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A homologation reaction of an aldehyde to yield a terminal alkyne. The reagents are tetrabromomethane, triphenylphosphine, butyllithium and water.
https://www.rsc.org/Merck-Index/reaction/r89/
https://www.wikidata.org/wiki/Q903573
Ramirez-Corey-Fuchs reaction
RXNO
RXNO:0000146
Corey-Fuchs reaction
A homologation reaction of an aldehyde to yield a terminal alkyne. The reagents are tetrabromomethane, triphenylphosphine, butyllithium and water.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A reduction of a quaternary ammonium salt containing at least one unsaturated substituent, to give a tertiary amine.
https://www.rsc.org/Merck-Index/reaction/r127/
https://www.wikidata.org/wiki/Q2026108
Emde reaction
Emde reduction
RXNO
RXNO:0000147
Emde degradation
A reduction of a quaternary ammonium salt containing at least one unsaturated substituent, to give a tertiary amine.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The [3,3]-sigmatropic rearrangement of an allyl vinyl ether to give a gamma,delta-unsaturated carbonyl compound.
https://www.rsc.org/Merck-Index/reaction/r80/
https://www.wikidata.org/wiki/Q900936
RXNO
RXNO:0000148
Claisen rearrangement
The [3,3]-sigmatropic rearrangement of an allyl vinyl ether to give a gamma,delta-unsaturated carbonyl compound.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The enolisation and subsequent [3,3]-sigmatropic rearrangement of an allylic acetate to give a gamma,delta-unsaturated carboxylic acid.
https://www.rsc.org/Merck-Index/reaction/r80/
https://www.wikidata.org/wiki/Q1945726
RXNO
RXNO:0000149
Ireland-Claisen rearrangement
The enolisation and subsequent [3,3]-sigmatropic rearrangement of an allylic acetate to give a gamma,delta-unsaturated carboxylic acid.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs.
RXNO
RXNO:0000150
joining with rearrangement
A reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs.
https://orcid.org/0000-0001-5985-7429
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.
RXNO
RXNO:0000151
Bellus-Claisen rearrangement
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r80/
RXNO
RXNO:0000152
Eschenmoser-Claisen rearrangement
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and trimethyl orthoacetate to give a gamma,delta-unsaturated alkyl ester.
https://www.rsc.org/Merck-Index/reaction/r80/
RXNO
RXNO:0000153
Johnson-Claisen rearrangement
The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and trimethyl orthoacetate to give a gamma,delta-unsaturated alkyl ester.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The oxidation of a primary alcohol or secondary alcohol to an aldehyde or ketone respectively. Does not work with allylic or benzylic alcohols.
https://www.rsc.org/Merck-Index/reaction/r426
RXNO
RXNO:0000154
Swern oxidation
The oxidation of a primary alcohol or secondary alcohol to an aldehyde or ketone respectively. Does not work with allylic or benzylic alcohols.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r141/
RXNO
RXNO:0000155
Finkelstein reaction
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The derivatisation (for example with tosyl chloride) and subsequent rearrangement of a hydroxamic acid to give an isocyanate.
https://www.rsc.org/Merck-Index/reaction/r259/
RXNO
RXNO:0000156
Lossen rearrangement
The derivatisation (for example with tosyl chloride) and subsequent rearrangement of a hydroxamic acid to give an isocyanate.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The conversion of a primary nitroalkane or secondary nitroalkane to an aldehyde or ketone, respectively.
https://www.rsc.org/Merck-Index/reaction/r297/
RXNO
RXNO:0000157
Nef reaction
The conversion of a primary nitroalkane or secondary nitroalkane to an aldehyde or ketone, respectively.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
RXNO
RXNO:0000158
Japp-Klingemann reaction
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The formation of a quinoline from a primary aromatic amine and an alpha,beta-unsaturated carbonyl compound.
Doebner-von Miller reaction
Skraup-Doebner-von Miller quinoline synthesis
RXNO
RXNO:0000159
Doebner-Miller reaction
The formation of a quinoline from a primary aromatic amine and an alpha,beta-unsaturated carbonyl compound.
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The protection of an amine (often a peptide) as its 9H-fluoren-9-ylmethoxycarbonyl derivative.
RXNO
RXNO:0000160
Fmoc protection
The protection of an amine (often a peptide) as its 9H-fluoren-9-ylmethoxycarbonyl derivative.
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The cyclisation of a 1,4-dicarbonyl compound with another molecule to give a five-membered aromatic ring compound.
RXNO
RXNO:0000161
Usually this gives rise to a heterocycle.
Paal-Knorr synthesis
The cyclisation of a 1,4-dicarbonyl compound with another molecule to give a five-membered aromatic ring compound.
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The cyclisation of a 1,4-dicarbonyl compound with an acid catalyst to give a furan.
https://www.rsc.org/Merck-Index/reaction/r315/
RXNO
RXNO:0000162
Paal-Knorr furan synthesis
The cyclisation of a 1,4-dicarbonyl compound with an acid catalyst to give a furan.
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The cyclisation of a 1,4-dicarbonyl compound with phosphorus pentasulfide to give a thiophene.
RXNO
RXNO:0000163
Paal-Knorr thiophene synthesis
The cyclisation of a 1,4-dicarbonyl compound with phosphorus pentasulfide to give a thiophene.
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The cyclisation of a 1,4-dicarbonyl compound with an amine to give a pyrrole.
https://www.rsc.org/Merck-Index/reaction/r316/
RXNO
RXNO:0000164
Merck Index says "ammonia or primary amines"
Paal-Knorr pyrrole synthesis
The cyclisation of a 1,4-dicarbonyl compound with an amine to give a pyrrole.
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r392/
RXNO
RXNO:0000165
Schotten-Baumann reaction
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The elimination of a methylated amine from an alkylamine to form an olefin. The reaction proceeds via the quaternary ammonium salt.
https://www.rsc.org/Merck-Index/reaction/r205/
exhaustive methylation
RXNO
Hofmann degradation
RXNO:0000166
Hofmann elimination
The elimination of a methylated amine from an alkylamine to form an olefin. The reaction proceeds via the quaternary ammonium salt.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The esterification of a carboxylic acid with an alcohol. Various Lewis acids or Bronsted acids may be used as catalyst.
Fischer esterification
RXNO
RXNO:0000167
Fischer-Speier esterification
The esterification of a carboxylic acid with an alcohol. Various Lewis acids or Bronsted acids may be used as catalyst.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
Weerman degradation
Weerman's reaction
RXNO
RXNO:0000168
Weerman reaction
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
RXNO
RXNO:0000169
Dakin reaction
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reaction of a carboxylic acid with hydrazoic acid to give the lower homologue amine, with the loss of the terminal carbon atom.
RXNO
RXNO:0000170
Schmidt rearrangement, carboxylic acid
The reaction of a carboxylic acid with hydrazoic acid to give the lower homologue amine, with the loss of the terminal carbon atom.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
RXNO
RXNO:0000171
Schmidt rearrangement, ketone
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reaction of a tertiary alcohol with hydrazoic acid with rearrangement to form an imide.
RXNO
RXNO:0000172
Schmidt rearrangement, tertiary alcohol
The reaction of a tertiary alcohol with hydrazoic acid with rearrangement to form an imide.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reaction of an alkene with hydrazoic acid with rearrangement to form an imide.
RXNO
RXNO:0000173
Schmidt rearrangement, alkene
The reaction of an alkene with hydrazoic acid with rearrangement to form an imide.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The [2,3]-sigmatropic rearrangement of a benzyl quaternary ammonium salt to form an aniline.
RXNO
RXNO:0000174
Sommelet-Hauser rearrangement
The [2,3]-sigmatropic rearrangement of a benzyl quaternary ammonium salt to form an aniline.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
RXNO
RXNO:0000175
Dakin-West reaction
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
RXNO
RXNO:0000176
Beckmann fragmentation
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The transfer of a hydrogen or halogen atom from a haloalkane to an alkene, giving the chain-extended halogenated alkane.
Kharasch addition reaction
RXNO
RXNO:0000177
Kharasch reaction
The transfer of a hydrogen or halogen atom from a haloalkane to an alkene, giving the chain-extended halogenated alkane.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
RXNO
RXNO:0000178
Kharasch-Sosnovsky reaction
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The oxidation of a phenol to give a (predominantly para) diphenol using potassium persulfate.
RXNO
RXNO:0000179
Elbs persulfate oxidation, phenol variant
The oxidation of a phenol to give a (predominantly para) diphenol using potassium persulfate.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The oxidation of a methyl-substituted aromatic compound to the corresponding benzaldehyde using potassium persulfate.
RXNO
RXNO:0000180
Elbs persulfate oxidation, tolyl variant
The oxidation of a methyl-substituted aromatic compound to the corresponding benzaldehyde using potassium persulfate.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r59/
RXNO
RXNO:0000181
Boyland-Sims oxidation
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The (predominantly ortho) carboxylation of a phenoxide.
https://www.rsc.org/Merck-Index/reaction/r239/
RXNO
RXNO:0000182
Kolbe-Schmitt reaction
The (predominantly ortho) carboxylation of a phenoxide.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reaction between an alpha-halocarbonyl compound and a trialkyl phosphite to give an enol phosphate.
https://www.rsc.org/Merck-Index/reaction/r329/
RXNO
RXNO:0000183
not clear why this is where it is and not a sibling of the Arbuzov reaction (2014-02-17)
Perkow reaction
The reaction between an alpha-halocarbonyl compound and a trialkyl phosphite to give an enol phosphate.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r335/
Moffatt oxidation
RXNO
RXNO:0000184
Pfitzner-Moffatt oxidation
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
RXNO
RXNO:0000185
Willgerodt reaction
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
https://www.rsc.org/Merck-Index/reaction/r466/
RXNO
RXNO:0000186
Willgerodt-Kindler reaction
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The formation of an ester from two aldehydes via a disproportionation process using a metal alkoxide to oxidise one aldehyde and reduce the other.
https://www.rsc.org/Merck-Index/reaction/r433/
RXNO
RXNO:0000187
Tishchenko reaction
The formation of an ester from two aldehydes via a disproportionation process using a metal alkoxide to oxidise one aldehyde and reduce the other.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The reaction between a methylene ketone and a polynitro aromatic compound.
https://www.rsc.org/Merck-Index/reaction/r482/
RXNO
RXNO:0000188
Zimmermann reaction
The reaction between a methylene ketone and a polynitro aromatic compound.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The rearrangement of the sulfonic ester of a ketoxime in base to give an alpha-amino ketone.
https://www.rsc.org/Merck-Index/reaction/r296/
RXNO
RXNO:0000189
Neber rearrangement
The rearrangement of the sulfonic ester of a ketoxime in base to give an alpha-amino ketone.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
true
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.
Nozaki reaction
Nozaki-Hiyama-Kishi coupling
Nozaki-Kishi reaction
RXNO
RXNO:0000191
Nozaki-Hiyama-Kishi reaction
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
Buchwald-Hartwig reaction
RXNO
RXNO:0000192
Buchwald-Hartwig amination
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction where an organosilane reacts with an organic halide or triflate. It is catalysed by a palladium or nickel complex.
Hiyama cross-coupling
RXNO
RXNO:0000193
Hiyama coupling
A carbon-carbon coupling reaction where an organosilane reacts with an organic halide or triflate. It is catalysed by a palladium or nickel complex.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
RXNO
RXNO:0000194
Stevens rearrangement
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The 1,2-rearrangement of an alpha-methylene ammonium salt to an amine in the presence of strong base.
RXNO
RXNO:0000195
Stevens rearrangement, ammonium
The 1,2-rearrangement of an alpha-methylene ammonium salt to an amine in the presence of strong base.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The 1,2-rearrangement of an alpha-methylene sulfonium salt to a sulfide in the presence of strong base.
RXNO
RXNO:0000196
Stevens rearrangement, sulfonium
The 1,2-rearrangement of an alpha-methylene sulfonium salt to a sulfide in the presence of strong base.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A [3,3]-sigmatropic rearrangement where an aza-1,5-hexadiene rearranges to form an aza-1,5-hexadiene.
RXNO
RXNO:0000197
aza-Cope rearrangement
A [3,3]-sigmatropic rearrangement where an aza-1,5-hexadiene rearranges to form an aza-1,5-hexadiene.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The rearrangement of a 2-aza-1,5-hexadiene to form an imine.
RXNO
RXNO:0000198
2-aza-Cope rearrangement
The rearrangement of a 2-aza-1,5-hexadiene to form an imine.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The rearrangement of a 3-aza-1,5-hexadiene to form a delta,epsilon-unsaturated imine.
amino-Claisen rearrangement
aza-Claisen rearrangement
RXNO
RXNO:0000199
This is the reverse of the 1-aza-Cope rearrangement.
3-aza-Cope rearrangement
The rearrangement of a 3-aza-1,5-hexadiene to form a delta,epsilon-unsaturated imine.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The rearrangement of a delta,epsilon-unsaturated imine to form a 3-aza-1,5-hexadiene.
RXNO
RXNO:0000200
This is the reverse of the 3-aza-Cope rearrangement.
1-aza-Cope rearrangement
The rearrangement of a delta,epsilon-unsaturated imine to form a 3-aza-1,5-hexadiene.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The rearrangement of an oxazolyl carbonate to a C-carboxyazlactone.
RXNO
RXNO:0000201
Steglich rearrangement
The rearrangement of an oxazolyl carbonate to a C-carboxyazlactone.
RSC:jrw
https://orcid.org/0000-0001-5985-7429
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.
RXNO
RXNO:0000202
ring rearrangement
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.
https://orcid.org/0000-0001-5985-7429
A reaction in which a protecting group is modified by converting it into a functional group.
NAMERXN:6
RXNO
RXNO:0000203
deprotection reaction
A reaction in which a protecting group is modified by converting it into a functional group.
https://orcid.org/0000-0001-5985-7429
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.
metathesis
multiple bond metathesis
RXNO
RXNO:0000204
multiple-bond metathesis
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.
https://orcid.org/0000-0001-5985-7429
A planned reaction step in which the product has fewer rings than the reactants.
ring opening
selective ring opening
RXNO
RXNO:0000205
ring breaking
A planned reaction step in which the product has fewer rings than the reactants.
https://orcid.org/0000-0001-5985-7429
A planned reaction step in which an existing ring is reduced in size.
RXNO
RXNO:0000206
ring contraction
A planned reaction step in which an existing ring is reduced in size.
https://orcid.org/0000-0001-5985-7429
An addition reaction between a carbonyl compound, an inorganic cyanide and an ammonium salt, followed by hydrolysis, to give an alpha-amino carboxylic acid.
RXNO
RXNO:0000207
Strecker reaction
An addition reaction between a carbonyl compound, an inorganic cyanide and an ammonium salt, followed by hydrolysis, to give an alpha-amino carboxylic acid.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The [3,3]-sigmatropic rearrangement, and subsequent re-aromatisation, of an allyl aryl ether to give an ortho-allyl phenol.
RXNO
RXNO:0000208
aromatic Claisen rearrangement
The [3,3]-sigmatropic rearrangement, and subsequent re-aromatisation, of an allyl aryl ether to give an ortho-allyl phenol.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The acid-catalysed cyclisation of a divinylketone to give a cyclopentenone.
https://www.rsc.org/Merck-Index/reaction/r295/
Nazarov cyclization
RXNO
RXNO:0000209
Nazarov cyclisation
The acid-catalysed cyclisation of a divinylketone to give a cyclopentenone.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The stereospecific oxidation of a (phenyldimethylsilyl)alkane to the corresponding alcohol using bromine, usually generated in situ from potassium bromide and peracetic acid.
https://www.rsc.org/Merck-Index/reaction/r150/
Fleming oxidation
Tamao-Fleming oxidation
RXNO
RXNO:0000210
Fleming-Tamao oxidation
The stereospecific oxidation of a (phenyldimethylsilyl)alkane to the corresponding alcohol using bromine, usually generated in situ from potassium bromide and peracetic acid.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The stereospecific oxidation of a (halosilyl)alkane to the corresponding alcohol using potassium fluoride and hydrogen peroxide.
https://www.rsc.org/Merck-Index/reaction/r150/
Tamao-Kumada oxidation
RXNO
RXNO:0000211
Tamao oxidation
The stereospecific oxidation of a (halosilyl)alkane to the corresponding alcohol using potassium fluoride and hydrogen peroxide.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction in which an aldehyde or ketone reacts with allyltrimethylsilane to form a homoallylic alcohol.
RXNO
RXNO:0000212
Sakurai reaction, aldehyde or ketone
A carbon-carbon coupling reaction in which an aldehyde or ketone reacts with allyltrimethylsilane to form a homoallylic alcohol.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction in which an enone reacts with allyltrimethylsilane to form a delta,epsilon-unsaturated carbonyl compound.
RXNO
RXNO:0000213
Sakurai reaction, enone
A carbon-carbon coupling reaction in which an enone reacts with allyltrimethylsilane to form a delta,epsilon-unsaturated carbonyl compound.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction in which an acid chloride reacts with allyltrimethylsilane to form a gamma,delta-unsaturated ketone.
RXNO
RXNO:0000214
Sakurai reaction, acid chloride
A carbon-carbon coupling reaction in which an acid chloride reacts with allyltrimethylsilane to form a gamma,delta-unsaturated ketone.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction in which an acetal or ketal reacts with allyltrimethylsilane to form a homoallylic ether.
RXNO
RXNO:0000215
Sakurai reaction, acetal or ketal
A carbon-carbon coupling reaction in which an acetal or ketal reacts with allyltrimethylsilane to form a homoallylic ether.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A carbon-carbon coupling reaction in which an imine reacts with allyltrimethylsilane to form a homoallylic amine.
RXNO
RXNO:0000216
imine Sakurai reaction
A carbon-carbon coupling reaction in which an imine reacts with allyltrimethylsilane to form a homoallylic amine.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
A ring-breaking reaction in which an epoxide reacts with allyltrimethylsilane to form a hydroxy alkene.
RXNO
RXNO:0000217
Sakurai reaction, epoxide
A ring-breaking reaction in which an epoxide reacts with allyltrimethylsilane to form a hydroxy alkene.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The disproportionation of a non-enolisable aldehyde to the corresponding carboxylic acid and alcohol. The reaction is base-catalysed.
https://www.rsc.org/Merck-Index/reaction/r71/
RXNO
RXNO:0000218
Cannizzaro reaction
The disproportionation of a non-enolisable aldehyde to the corresponding carboxylic acid and alcohol. The reaction is base-catalysed.
RSC:db
https://orcid.org/0000-0002-4077-4719
The reaction between two different non-enolisable aldehydes to give a carboxylic acid and an alcohol. The reaction is base-catalysed.
https://www.rsc.org/Merck-Index/reaction/r71/
RXNO
RXNO:0000219
crossed Cannizzaro reaction
The reaction between two different non-enolisable aldehydes to give a carboxylic acid and an alcohol. The reaction is base-catalysed.
RSC:db
https://orcid.org/0000-0002-4077-4719
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.
Pummerer methyl sulfoxide rearrangement
RXNO
RXNO:0000220
Pummerer rearrangement
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
The reaction of a tertiary amine oxide with an anhydride or acyl chloride to give an N,N-disubstituted acetamide and an aldehyde.
RXNO
RXNO:0000221
Polonovski reaction
The reaction of a tertiary amine oxide with an anhydride or acyl chloride to give an N,N-disubstituted acetamide and an aldehyde.
RSC:db
https://orcid.org/0000-0002-4077-4719
The reaction of a tertiary amine oxide with trifluoroacetic anhydride to give an N,N-disubstituted acetamide and an aldehyde.
Potier-Polonovski reaction
RXNO
RXNO:0000222
Polonovski-Potier reaction
The reaction of a tertiary amine oxide with trifluoroacetic anhydride to give an N,N-disubstituted acetamide and an aldehyde.
RSC:db
https://orcid.org/0000-0002-4077-4719
The alkylation of a tertiary amine with an alkyl halide to the corresponding ammonium salt.
RXNO:0000375
https://www.rsc.org/Merck-Index/reaction/r275/
Menschutkin reaction
RXNO
RXNO:0000223
Menshutkin reaction
The alkylation of a tertiary amine with an alkyl halide to the corresponding ammonium salt.
RSC:db
https://orcid.org/0000-0002-4077-4719
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.
RXNO
RXNO:0000224
Strecker degradation
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.
RSC:db
https://orcid.org/0000-0002-4077-4719
The allylic or benzylic bromination of hydrocarbons using an N-bromoimide and a radical initiator, to give an allylic or benzylic bromide.
Wohl-Ziegler reaction
RXNO
RXNO:0000225
Wohl-Ziegler bromination
The allylic or benzylic bromination of hydrocarbons using an N-bromoimide and a radical initiator, to give an allylic or benzylic bromide.
RSC:db
https://orcid.org/0000-0002-4077-4719
The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base.
RXNO
RXNO:0000226
Wolff-Kishner reduction
The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base.
RSC:db
https://orcid.org/0000-0002-4077-4719
The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base in refluxing ethylene glycol.
Huang-Minlon modification
RXNO
RXNO:0000227
Wolff-Kishner reduction, Huang-Minlon modification
The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base in refluxing ethylene glycol.
RSC:db
https://orcid.org/0000-0002-4077-4719
The reduction of an ester to the corresponding alcohol, using sodium methoxide in dry methanol.
Zemplen procedure
RXNO
RXNO:0000228
Zemplen transesterification
The reduction of an ester to the corresponding alcohol, using sodium methoxide in dry methanol.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The rearrangement of an O-alkenyl acetal to give the corresponding beta-alkoxy carbonyl compound.
Ferrier reaction
RXNO
RXNO:0000229
Ferrier rearrangement
The rearrangement of an O-alkenyl acetal to give the corresponding beta-alkoxy carbonyl compound.
https://orcid.org/0000-0002-4077-4719
The rearrangement of an O-alkenyl hemiaminal ether to give the corresponding beta-amino carbonyl compound.
aza-Ferrier reaction
RXNO
RXNO:0000230
aza-Ferrier rearrangement
The rearrangement of an O-alkenyl hemiaminal ether to give the corresponding beta-amino carbonyl compound.
https://orcid.org/0000-0002-4077-4719
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.
RXNO
RXNO:0000231
aza-ene reaction
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.
https://orcid.org/0000-0001-5985-7429
The alkylation of an amine with a boronic acid and an aldehyde to give a substituted amine.
Petasis three-component coupling
RXNO
RXNO:0000232
Petasis reaction
The alkylation of an amine with a boronic acid and an aldehyde to give a substituted amine.
RSC:db
A rearrangement of a furfuryl alcohol derivative to a dihydropyranone, from which monosaccharides may be synthesised.
RXNO
RXNO:0000233
Achmatowicz rearrangement
A rearrangement of a furfuryl alcohol derivative to a dihydropyranone, from which monosaccharides may be synthesised.
RSC:db
A rearrangement of a furfuryl amine derivative to a tetrahydropyridinone.
RXNO
RXNO:0000234
aza-Achmatowicz rearrangement
A rearrangement of a furfuryl amine derivative to a tetrahydropyridinone.
RSC:db
A carbon-carbon coupling reaction between a nitroalkane and an imine to give a beta-amino nitroalkane.
RXNO
RXNO:0000235
aza-Henry reaction
A carbon-carbon coupling reaction between a nitroalkane and an imine to give a beta-amino nitroalkane.
RSC:db
A three-component coupling of a beta-keto ester, an aldehyde and urea to give a 3,4-dihydropyrimidinone.
https://www.rsc.org/Merck-Index/reaction/r43/
Biginelli condensation
Biginelli pyrimidone synthesis
Biginelli three-component reaction
RXNO
RXNO:0000236
Biginelli reaction
A three-component coupling of a beta-keto ester, an aldehyde and urea to give a 3,4-dihydropyrimidinone.
RSC:db
The coupling of an alpha-bromo ester with a nitrile to give a beta-ketoester, in the presence of zinc.
RXNO
RXNO:0000237
Blaise reaction
The coupling of an alpha-bromo ester with a nitrile to give a beta-ketoester, in the presence of zinc.
RSC:db
The substitution of an amine with a nucleophile using a pyrylium salt.
RXNO
RXNO:0000238
Katritzky pyrylium-pyridinium method
The substitution of an amine with a nucleophile using a pyrylium salt.
https://orcid.org/0000-0002-4077-4719
The rearrangement of a 3-aza-4-metalla-1,5-hexadiene to form a delta,epsilon-unsaturated metallaimine.
RXNO
RXNO:0000239
metalla-aza-Claisen rearrangement
The rearrangement of a 3-aza-4-metalla-1,5-hexadiene to form a delta,epsilon-unsaturated metallaimine.
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
The cyclisation of an ene-diyne to give a 1,4-diradical cyclohexatriene. The diradical usually aromatises.
https://www.rsc.org/Merck-Index/reaction/r37/
Bergman cyclization
Bergman reaction
Masamune-Bergman cyclisation
Masamune-Bergman cyclization
RXNO
RXNO:0000240
Bergman cyclisation
The cyclisation of an ene-diyne to give a 1,4-diradical cyclohexatriene. The diradical usually aromatises.
https://orcid.org/0000-0002-4077-4719
A conjugate addition reaction where a carbon nucleophile adds to an alpha,beta-unsaturated nitro compound.
RXNO
RXNO:0000241
nitro-Michael reaction
A conjugate addition reaction where a carbon nucleophile adds to an alpha,beta-unsaturated nitro compound.
https://orcid.org/0000-0002-4077-4719
The homogeneous asymmetric catalytic hydrogenation of a C=C double bond using a ruthenium(II) BINAP catalyst.
Noyori hydrogenation, alkene
RXNO
RXNO:0000242
Noyori asymmetric hydrogenation, alkene
The homogeneous asymmetric catalytic hydrogenation of a C=C double bond using a ruthenium(II) BINAP catalyst.
https://orcid.org/0000-0002-4077-4719
The homogeneous asymmetric catalytic hydrogenation of a carbonyl bond using a ruthenium(II) BINAP catalyst.
Noyori hydrogenation, carbonyl
RXNO
RXNO:0000243
Noyori asymmetric hydrogenation, carbonyl
The homogeneous asymmetric catalytic hydrogenation of a carbonyl bond using a ruthenium(II) BINAP catalyst.
https://orcid.org/0000-0002-4077-4719
The reaction between an isonitrile, a carboxylic acid and aldehyde or ketone to give an alpha-acyloxy amide.
RXNO
RXNO:0000244
Passerini reaction
The reaction between an isonitrile, a carboxylic acid and aldehyde or ketone to give an alpha-acyloxy amide.
https://orcid.org/0000-0002-4077-4719
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.
RCM
ring closing alkene metathesis
ring closing metathesis
ring closing olefin metathesis
ring-closing alkene metathesis
ring-closing olefin metathesis
RXNO
RXNO:0000245
ring-closing metathesis
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.
https://orcid.org/0000-0002-4077-4719
A joining reaction, the objective of which is that a large number of monomers react together to produce a polymer consisting of repeating units.
polymerisation
polymerization
polymerization reaction
RXNO
RXNO:0000246
polymerisation reaction
A joining reaction, the objective of which is that a large number of monomers react together to produce a polymer consisting of repeating units.
rsc:db
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.
ROMP
ring-opening metathesis polymerization
RXNO
RXNO:0000247
ring-opening metathesis polymerisation
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.
https://orcid.org/0000-0002-4077-4719
rsc:db
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.
https://www.rsc.org/Merck-Index/reaction/r72/
Kimel-Cope rearrangement
RXNO
RXNO:0000248
Carroll rearrangement
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.
RSC:db
A Mitsunobu reaction, where an alcohol is converted to something else with inversion at the stereocentre, using diphenylphosphoryl azide.
RXNO
RXNO:0000249
Bose-Mitsunobu reaction
A Mitsunobu reaction, where an alcohol is converted to something else with inversion at the stereocentre, using diphenylphosphoryl azide.
RSC:db
The rearrangement of a 2-bromoalkene into an alkyne, mediated by strong base.
https://www.rsc.org/Merck-Index/reaction/r161/
https://www.wikidata.org/wiki/Q573664
RXNO
RXNO:0000250
Fritsch-Buttenberg-Wiechell rearrangement
The rearrangement of a 2-bromoalkene into an alkyne, mediated by strong base.
RSC:db
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.
RXNO
RXNO:0000251
Stork-Wittig olefination
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.
RSC:db
The reduction of a 2-nitrobiaryl compound to give a carbazole.
RXNO
RXNO:0000252
Cadogan carbazole synthesis
The reduction of a 2-nitrobiaryl compound to give a carbazole.
doi:10.1039/JR9650004831
https://orcid.org/0000-0002-4077-4719
The arylation of an arylamine mediated by isopentyl nitrite.
RXNO
RXNO:0000253
Cadogan coupling
The arylation of an arylamine mediated by isopentyl nitrite.
doi:10.1039/b409373a
https://orcid.org/0000-0002-4077-4719
The reaction between a 1,9-diformyldipyrromethane and a dipyrromethane to give a porphodimethene.
RXNO
RXNO:0000254
MacDonald condensation
The reaction between a 1,9-diformyldipyrromethane and a dipyrromethane to give a porphodimethene.
doi:10.1039/a908784b
https://orcid.org/0000-0002-4077-4719
The carbon-carbon homocoupling reaction of a pair of alkyne molecules using a borane and iodine. The reaction proceeds via a borane intermediate.
RXNO
RXNO:0000255
Zweifel diene synthesis
The carbon-carbon homocoupling reaction of a pair of alkyne molecules using a borane and iodine. The reaction proceeds via a borane intermediate.
https://orcid.org/0000-0002-4077-4719
isbn:9780521096430
The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using the Dess-Martin periodinane.
https://www.rsc.org/Merck-Index/reaction/r107/
https://www.wikidata.org/wiki/Q28455131
Dess-Martin periodinane oxidation
RXNO
RXNO:0000256
Dess-Martin oxidation
The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using the Dess-Martin periodinane.
https://orcid.org/0000-0001-5985-7429
The oxidative cleavage of an alpha,beta-diol using lead tetraacetate to give the corresponding carbonyl compounds.
https://www.rsc.org/Merck-Index/reaction/r96/
https://www.wikidata.org/wiki/Q30693026
Criegee glycol cleavage
Criegee reaction
RXNO
RXNO:0000257
Criegee oxidation
The oxidative cleavage of an alpha,beta-diol using lead tetraacetate to give the corresponding carbonyl compounds.
https://orcid.org/0000-0001-5985-7429
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.
https://www.rsc.org/Merck-Index/reaction/r400/
https://www.wikidata.org/wiki/Q903776
Simmons-Smith cyclopropanation
RXNO
RXNO:0000258
Simmons-Smith reaction
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.
RSC:db
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
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.
RXNO
RXNO:0000259
Wittig rearrangement
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.
https://orcid.org/0000-0001-5985-7429
https://orcid.org/0000-0002-4077-4719
rsc:db
A base-mediated 1,2-sigmatropic rearrangement of an ether to give an alcohol.
1,2-Wittig rearrangement
[1,2] Wittig rearrangement
RXNO
RXNO:0000260
[1,2]-Wittig rearrangement
A base-mediated 1,2-sigmatropic rearrangement of an ether to give an alcohol.
rsc:db
A base-mediated 2,3-sigmatropic rearrangement of an allyl ether to give a homoallylic alcohol.
2,3-Wittig rearrangement
[2,3] Wittig rearrangement
RXNO
RXNO:0000261
[2,3]-Wittig rearrangement
A base-mediated 2,3-sigmatropic rearrangement of an allyl ether to give a homoallylic alcohol.
rsc:db
A base-mediated 1,2-sigmatropic rearrangement of a tertiary amine to give a secondary amine.
1,2-aza-Wittig rearrangement
[1,2] aza-Wittig rearrangement
RXNO
RXNO:0000262
[1,2]-aza-Wittig rearrangement
A base-mediated 1,2-sigmatropic rearrangement of a tertiary amine to give a secondary amine.
rsc:db
A base-mediated 2,3-sigmatropic rearrangement of an activated tertiary allyl amine, to give a secondary homoallylic amine.
2,3-aza-Wittig rearrangement
[2,3] aza-Wittig rearrangement
RXNO
RXNO:0000263
[2,3]-aza-Wittig rearrangement
A base-mediated 2,3-sigmatropic rearrangement of an activated tertiary allyl amine, to give a secondary homoallylic amine.
rsc:db
A carbon-carbon coupling of an imine to an activated alkene in the presence of a nucleophilic base to give an allylic amine.
aza-Morita-Baylis-Hillman reaction
RXNO
RXNO:0000264
aza-Baylis-Hillman reaction
A carbon-carbon coupling of an imine to an activated alkene in the presence of a nucleophilic base to give an allylic amine.
rsc:db
Reaction of a carbonyl compound with a phosphazene to give an imine.
RXNO
RXNO:0000265
aza-Wittig reaction
Reaction of a carbonyl compound with a phosphazene to give an imine.
rsc:db
An oxidation reaction involving Fenton's reagent.
RXNO:0000267
Fenton's reaction
RXNO
RXNO:0000266
Fenton reaction
An oxidation reaction involving Fenton's reagent.
https://orcid.org/0000-0001-5985-7429
true
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.
Hantzsch dihydropyridine synthesis
RXNO
RXNO:0000268
Hantzsch pyridine synthesis
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.
rsc:db
A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole, needing only heat to proceed.
Huisgen cycloaddition
Huisgen reaction
Huisgen's 1,3-dipolar cycloaddition
"click" reaction
'click' reaction
alkyne-azide Huisgen cycloaddition
alkyne-azide Huisgen reaction
azide-alkyne Huisgen cycloaddition
azide-alkyne Huisgen reaction
azide-alkyne click reaction
click reaction
RXNO
RXNO:0000269
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.
alkyne-azide click reaction
A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole, needing only heat to proceed.
rsc:db
A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole as a single regioisomer.
CuAAC
copper(I)-catalysed alkyne-azide cycloaddition
copper(I)-catalysed azide-alkyne click reaction
copper(I)-catalysed azide-alkyne cycloaddition
copper(I)-catalyzed alkyne-azide cycloaddition
copper(I)-catalyzed azide-alkyne click reaction
copper(I)-catalyzed azide-alkyne cycloaddition
RXNO
RXNO:0000270
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]
copper(I)-catalyzed azide-alkyne cycloaddition
A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole as a single regioisomer.
RSC:db
A process in which carbon monoxide and hydrogen ('syngas') are converted into various liquid hydrocarbons.
Fischer-Tropsch reaction
Fischer-Tropsch synthesis
RXNO
RXNO:0000271
Fischer-Tropsch process
A process in which carbon monoxide and hydrogen ('syngas') are converted into various liquid hydrocarbons.
rsc:db
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.
RXNO
RXNO:0000272
hydroformylation
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.
rsc:db
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).
retro Diels-Alder reaction
RXNO
RXNO:0000273
retro-Diels-Alder reaction
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).
rsc:db
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.
retro-aldol reaction
RXNO
RXNO:0000274
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.
retro-aldol addition
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.
rsc:db
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.
RXNO
RXNO:0000275
Stork-Crabtree hydrogenation
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.
doi:10.1021/jo00364a007
rsc:db
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.
"Aufbau" reaction
'Aufbau' reaction
Aufbau process
RXNO
RXNO:0000276
Aufbau reaction
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.
rsc:db
The reaction of an aluminium alkyl with an alkene, to give an intermediate aluminium species that can give various products after work-up.
RXNO
RXNO:0000277
hydroalumination
The reaction of an aluminium alkyl with an alkene, to give an intermediate aluminium species that can give various products after work-up.
rsc:db
The reaction of two alkenes to give an elongated alkene, employing a transition-metal-based catalyst.
1,2-hydrovinylation
RXNO
RXNO:0000278
hydrovinylation
The reaction of two alkenes to give an elongated alkene, employing a transition-metal-based catalyst.
rsc:db
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).
RXNO
RXNO:0000279
1,4-hydrovinylation
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).
rsc:db
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.
Grubbs metathesis
Grubbs reaction
cross metathesis
cross-metathesis
olefin metathesis
transalkylidenation
RXNO
RXNO:0000280
alkene metathesis
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.
rsc:db
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.
RXNO
RXNO:0000281
alkyne metathesis
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.
rsc:db
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.
RXNO
RXNO:0000282
enyne metathesis
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.
rsc:db
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.
ring closing enyne metathesis
RXNO
RXNO:0000283
ring-closing enyne metathesis
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.
rsc:db
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.
ring opening metathesis
RXNO
RXNO:0000284
ring-opening metathesis
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.
rsc:db
A carbon-carbon coupling reaction where an aldehyde or ketone reacts with an allyl halide and zinc to give a homoallylic alcohol.
RXNO
RXNO:0000285
Not to be confused with the Luche reduction (the chemoselective reduction of an enone to an allylic alcohol).
Luche reaction
A carbon-carbon coupling reaction where an aldehyde or ketone reacts with an allyl halide and zinc to give a homoallylic alcohol.
https://orcid.org/0000-0002-4077-4719
rsc:db
The chemoselective reduction of an enone to give an allylic alcohol, using sodium borohydride and an lanthanoid chloride, typically cerium chloride.
RXNO
RXNO:0000286
Not to be confused with the Luche reaction (the coupling of an aldehyde or ketone with an allyl halide).
Luche reduction
The chemoselective reduction of an enone to give an allylic alcohol, using sodium borohydride and an lanthanoid chloride, typically cerium chloride.
https://orcid.org/0000-0002-4077-4719
rsc:db
The oxidation of an aldehyde to a carboxylic acid with chlorite.
RXNO
RXNO:0000287
Lindgren oxidation
The oxidation of an aldehyde to a carboxylic acid with chlorite.
doi:10.3891/acta.chem.scand.27-0888
https://orcid.org/0000-0002-4077-4719
rsc:db
A carbon-carbon coupling reaction where an aryl halide reacts with copper(I) cyanide to give an aryl nitrile.
https://www.rsc.org/Merck-Index/reaction/r376/
Rosenmund-von Braun synthesis
RXNO
RXNO:0000288
Rosenmund-von Braun reaction
A carbon-carbon coupling reaction where an aryl halide reacts with copper(I) cyanide to give an aryl nitrile.
https://orcid.org/0000-0002-4077-4719
rsc:db
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.
Woehler synthesis
Wohler reaction
Wohler synthesis
RXNO
RXNO:0000289
Woehler reaction
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.
https://orcid.org/0000-0002-4077-4719
rsc:db
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.
hydrosilation
RXNO
RXNO:0000290
hydrosilylation
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.
https://orcid.org/0000-0002-4077-4719
rsc:db
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.
RXNO
RXNO:0000291
hydroamination
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.
https://orcid.org/0000-0002-4077-4719
rsc:db
The addition of a boron hydride across a double bond of an alkene or alkyne. The boron usually adds to the less substituted carbon.
RXNO
RXNO:0000292
hydroboration
The addition of a boron hydride across a double bond of an alkene or alkyne. The boron usually adds to the less substituted carbon.
https://orcid.org/0000-0002-4077-4719
rsc:db
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.
RXNO
RXNO:0000293
hydroboration-oxidation
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.
https://orcid.org/0000-0002-4077-4719
rsc:db
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.
hydrometalation
RXNO
RXNO:0000294
hydrometallation
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.
https://orcid.org/0000-0002-4077-4719
rsc:db
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.
RXNO
RXNO:0000295
hydrozirconation
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.
https://orcid.org/0000-0002-4077-4719
rsc:db
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.
RXNO
RXNO:0000296
hydrostannylation
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.
https://orcid.org/0000-0002-4077-4719
rsc:db
The reaction of a organotellurium hydride with an alkyne, to give a (usually (Z)-configured) vinyltellurium species.
RXNO
RXNO:0000297
hydrotelluration
The reaction of a organotellurium hydride with an alkyne, to give a (usually (Z)-configured) vinyltellurium species.
https://orcid.org/0000-0002-4077-4719
rsc:db
The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using Fetizon's reagent.
RXNO
RXNO:0000298
Fetizon oxidation
The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using Fetizon's reagent.
:cg
rsc:db
The substitution of an acylated sugar with a silylated base to give a nucleoside.
Vorbrueggen glycosylation
Vorbruggen condensation
Vorbruggen glycosylation
RXNO
RXNO:0000299
Vorbrueggen condensation
The substitution of an acylated sugar with a silylated base to give a nucleoside.
:
https://orcid.org/0000-0002-4077-4719
rsc:db
The addition of a thiol across the double bond of an alkene to give a thioether.
thiol-ene click reaction
RXNO
RXNO:0000300
thiol-ene reaction
The addition of a thiol across the double bond of an alkene to give a thioether.
:cg
rsc:db
The nickel-catalysed carbon-carbon coupling of a dihaloaromatic compound or aromatic bistriflate to give a polymer.
Yamamoto coupling
Yamamoto polymerization
RXNO
RXNO:0000301
Yamamoto polymerisation
The nickel-catalysed carbon-carbon coupling of a dihaloaromatic compound or aromatic bistriflate to give a polymer.
https://orcid.org/0000-0002-4077-4719
rsc:db
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.
RXNO
RXNO:0000302
thermal hydrosilylation
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.
:cg
rsc:db
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.
photo-hydrosilylation
RXNO
RXNO:0000303
photohydrosilylation
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.
:cg
rsc:db
A carbon-carbon coupling reaction between a tetrazole sulfone and an aldehyde or ketone to give a (typically trans) alkene.
Julia-Kocienski coupling
Julia-Kocienski reaction
RXNO
RXNO:0000304
Julia-Kocienski olefination
A carbon-carbon coupling reaction between a tetrazole sulfone and an aldehyde or ketone to give a (typically trans) alkene.
rsc:db
The conversion of a selenoxide with an alpha-hydrogen to an alpha-subtituted selenoether.
selenoxide Pummerer reaction
RXNO
RXNO:0000305
seleno-Pummerer rearrangement
The conversion of a selenoxide with an alpha-hydrogen to an alpha-subtituted selenoether.
rsc:db
A carbon-carbon coupling reaction where an organohalide or triflate couples to an alkene in the same molecule, catalysed by palladium.
intramolecular Heck-Mizoroki
RXNO
RXNO:0000306
intramolecular Heck reaction
A carbon-carbon coupling reaction where an organohalide or triflate couples to an alkene in the same molecule, catalysed by palladium.
rsc:db
An intramolecular Heck reaction of an ortho-halo-aniline with an alkene, catalysed by palladium.
Mori-Ban indole reaction
RXNO
RXNO:0000307
Mori-Ban indole synthesis
An intramolecular Heck reaction of an ortho-halo-aniline with an alkene, catalysed by palladium.
rsc:db
The intramolecular esterification of a carboxylic acid group with an alcohol group using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent) - an intramolecular Yamaguchi esterification.
Yamaguchi lactonization
RXNO
RXNO:0000308
Yamaguchi lactonisation
The intramolecular esterification of a carboxylic acid group with an alcohol group using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent) - an intramolecular Yamaguchi esterification.
rsc:db
The esterification of a carboxylic acid with an alcohol using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent).
https://www.rsc.org/Merck-Index/reaction/r479/
RXNO
RXNO:0000309
Yamaguchi esterification
The esterification of a carboxylic acid with an alcohol using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent).
rsc:db
A Diels-Alder reaction between a diene and an aldehyde or ketone to give a six-membered oxygen-containing ring compound.
oxa Diels-Alder cycloaddition
oxa Diels-Alder reaction
oxa-Diels-Alder cycloaddition
oxo Diels-Alder cycloaddition
oxo Diels-Alder reaction
oxo-Diels-Alder cycloaddition
oxo-Diels-Alder reaction
RXNO
RXNO:0000310
oxa-Diels-Alder reaction
A Diels-Alder reaction between a diene and an aldehyde or ketone to give a six-membered oxygen-containing ring compound.
rsc:db
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).
Trost allylation
RXNO
RXNO:0000311
Tsuji-Trost reaction
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).
rsc:db
A ring rearrangement reaction where an amine reacts with a 2,5-dialkoxytetrahydrofuran to give a pyrrole.
Clauson-Kaas pyrrole synthesis
RXNO
RXNO:0000312
Clauson-Kaas reaction
A ring rearrangement reaction where an amine reacts with a 2,5-dialkoxytetrahydrofuran to give a pyrrole.
http://www.clauson-kaas.com/cgi-files/mdmgfx/file-709-116554-7465.pdf
A [4+2] cycloaddition reaction where a diene (or heterocyclic analogue) reacts with a dienophile to form an unsaturated heterocyclic six-membered ring compound.
RXNO
RXNO:0000313
hetero-Diels-Alder reaction
A [4+2] cycloaddition reaction where a diene (or heterocyclic analogue) reacts with a dienophile to form an unsaturated heterocyclic six-membered ring compound.
rsc:djb
true
true
A carbon-carbon coupling reaction that is catalysed by a palladium atom.
RXNO
RXNO:0000316
palladium-catalysed carbon-carbon coupling reaction
A carbon-carbon coupling reaction that is catalysed by a palladium atom.
https://orcid.org/0000-0001-5985-7429
A condensation reaction that results in the production of an ester.
NAMERXN:3.6
RXNO
RXNO:0000317
ester condensation reaction
A condensation reaction that results in the production of an ester.
https://orcid.org/0000-0001-5985-7429
true
true
A deprotection reaction where the reactive centre is an amino nitrogen atom.
RXNO
RXNO:0000320
amino group deprotection
A deprotection reaction where the reactive centre is an amino nitrogen atom.
https://orcid.org/0000-0001-5985-7429
A protection reaction where the reactive centre is an amino nitrogen atom.
RXNO
RXNO:0000321
amino group protection
A protection reaction where the reactive centre is an amino nitrogen atom.
https://orcid.org/0000-0001-5985-7429
An amino group protection where the amino nitrogen atom is protected by reaction with benzylamine.
RXNO
RXNO:0000322
benzylamine protection
An amino group protection where the amino nitrogen atom is protected by reaction with benzylamine.
https://orcid.org/0000-0001-5985-7429
A protection reaction where the reactive centre is a hydroxyl oxygen atom.
RXNO
RXNO:0000323
hydroxyl group protection
A protection reaction where the reactive centre is a hydroxyl oxygen atom.
https://orcid.org/0000-0001-5985-7429
A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a benzyl ether.
RXNO
RXNO:0000324
benzyl ether protection
A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a benzyl ether.
https://orcid.org/0000-0001-5985-7429
A protection reaction where the reactive centre is a carboxy oxygen.
RXNO
RXNO:0000325
carboxylic acid protection
A protection reaction where the reactive centre is a carboxy oxygen.
https://orcid.org/0000-0001-5985-7429
An amino group deprotection reaction where a tertbutoxycarbonyl group is removed in acid conditions.
RXNO
RXNO:0000326
Boc deprotection
An amino group deprotection reaction where a tertbutoxycarbonyl group is removed in acid conditions.
https://orcid.org/0000-0001-5985-7429
An amino group deprotection reaction where a benzylamine group is removed by hydrogenation.
RXNO
RXNO:0000327
benzylamine deprotection
An amino group deprotection reaction where a benzylamine group is removed by hydrogenation.
https://orcid.org/0000-0001-5985-7429
A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a silyl ether.
RXNO
RXNO:0000328
silyl protection
A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a silyl ether.
https://orcid.org/0000-0001-5985-7429
An experimental procedure with the aim of producing a portion of a given compound or mixture.
RXNO
RXNO:0000329
planned synthesis
An experimental procedure with the aim of producing a portion of a given compound or mixture.
https://orcid.org/0000-0001-5985-7429
A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of an acetate ester.
O-Ac protection
RXNO
RXNO:0000330
acetate protection
A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of an acetate ester.
https://orcid.org/0000-0001-5985-7429
A functional modification step in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent.
RXNO
RXNO:0000331
substitution step
A functional modification step in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent.
https://orcid.org/0000-0001-5985-7429
A substitution step where one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent.
RXNO
RXNO:0000332
aromatic substitution step
A substitution step where one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent.
https://orcid.org/0000-0001-5985-7429
An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide to form an aromatic halide.
RXNO
RXNO:0000333
Sandmeyer halogenation
An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide to form an aromatic halide.
RSC:db
An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) pseudohalide to form an aromatic pseudohalide.
RXNO
RXNO:0000334
Sandmeyer pseudohalogenation
An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) pseudohalide to form an aromatic pseudohalide.
RSC:db
A functional group modification where a carbonyl oxygen is replaced by an amine.
batchelorc
2012-03-22T12:15:29Z