RXNO is the name reaction ontology. It contains more than 500 classes representing organic reactions such as the Diels–Alder cyclization. RXNO RXNO 1.2 definition 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 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 RXNO CHEBI:15379 dioxygen RXNO CHEBI:15734 primary alcohol RXNO CHEBI:16227 pyridine RXNO CHEBI:16240 hydrogen peroxide RXNO CHEBI:16526 carbon dioxide RXNO CHEBI:16670 peptide RXNO CHEBI:16842 formaldehyde RXNO CHEBI:17087 ketone RXNO CHEBI:17478 aldehyde RXNO CHEBI:17883 hydrogen chloride RXNO CHEBI:18379 nitrile RXNO CHEBI:22213 acridines RXNO CHEBI:22495 arenecarbaldehyde RXNO CHEBI:22680 azide RXNO CHEBI:22698 benzaldehydes RXNO CHEBI:22715 benzimidazoles RXNO CHEBI:22929 bromoalkane RXNO CHEBI:23086 chalcones RXNO CHEBI:23128 chloroalkane RXNO CHEBI:23252 cinnamic acids RXNO CHEBI:23367 molecular entity 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 RXNO CHEBI:24828 indoles RXNO CHEBI:25000 lactone RXNO CHEBI:25698 ether RXNO CHEBI:25710 organophosphorus compound RXNO CHEBI:25717 organotin compound RXNO CHEBI:25750 oxime RXNO CHEBI:25996 phenylhydrazine RXNO CHEBI:26410 pyrazoles RXNO CHEBI:26421 pyridines RXNO CHEBI:26455 pyrroles RXNO CHEBI:26513 quinolines RXNO CHEBI:26588 triazines RXNO CHEBI:26708 sodium atom RXNO CHEBI:26878 tertiary alcohol RXNO CHEBI:26961 thiophenes 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 RXNO CHEBI:29785 nitro group RXNO CHEBI:30879 alcohol 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 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 RXNO CHEBI:33521 metal atom RXNO CHEBI:33575 carboxylic acid RXNO CHEBI:33595 cyclic compound RXNO CHEBI:33641 olefin RXNO CHEBI:33658 arene RXNO CHEBI:33822 organic hydroxy compound RXNO CHEBI:33823 enol RXNO CHEBI:33839 macromolecule RXNO CHEBI:33853 phenols RXNO CHEBI:33860 aromatic amine RXNO CHEBI:35255 chloroform RXNO CHEBI:35293 fused compound RXNO CHEBI:35352 organonitrogen compound 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 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:36684 organohalogen compound RXNO CHEBI:36687 acyl chloride RXNO CHEBI:36823 pseudohalo group RXNO CHEBI:36963 organooxygen compound RXNO CHEBI:37148 bromoarene RXNO CHEBI:37579 acyl halide RXNO CHEBI:37592 organic phosphonate RXNO CHEBI:37602 allenes RXNO CHEBI:37613 cyclohexadiene RXNO CHEBI:37622 carboxamide RXNO CHEBI:37757 iodoalkane RXNO CHEBI:38101 azacycle RXNO CHEBI:38104 oxacycle thiacycle RXNO CHEBI:38106 I think this is the same as a thiacycle but need to check. organosulfur heterocyclic compound RXNO CHEBI:38269 boronic acids RXNO CHEBI:38597 triazole RXNO CHEBI:38757 isoflavones RXNO CHEBI:38784 oxetanes RXNO CHEBI:39141 Brønsted acid RXNO CHEBI:39142 Brønsted base RXNO CHEBI:39143 Lewis acid RXNO CHEBI:39144 Lewis base RXNO CHEBI:39447 pyrimidines RXNO CHEBI:42485 formyl group RXNO CHEBI:43176 hydroxy group RXNO CHEBI:46882 amino group RXNO CHEBI:46883 carboxy group RXNO CHEBI:47266 hydrogen bromide RXNO CHEBI:47875 tetrabromomethane RXNO CHEBI:48420 chromium trioxide RXNO CHEBI:48513 carbazoles RXNO CHEBI:49553 copper(II) chloride RXNO CHEBI:50075 dihydropyridine RXNO CHEBI:50784 pivalate ester RXNO CHEBI:50887 haloarene RXNO CHEBI:50888 fluoroarene RXNO CHEBI:51080 nitrate ester RXNO CHEBI:51142 amino groups RXNO CHEBI:51154 phosphonium ylide RXNO CHEBI:51236 organomagnesium halide RXNO CHEBI:51454 cyclopropanes RXNO CHEBI:51721 alpha,beta-unsaturated ketone RXNO CHEBI:51849 beta-ketoester RXNO CHEBI:51929 arylacetylene RXNO CHEBI:52094 peroxy acid RXNO CHEBI:53212 isocyanates RXNO CHEBI:53434 palladium(II) chloride RXNO CHEBI:55380 beta-hydroxy ketone RXNO CHEBI:5686 heterocyclic compound RXNO CHEBI:59656 phosphine oxide RXNO CHEBI:59831 enyne 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 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 formaldehyde 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 formaldehyde 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 formaldehyde 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 formaldehyde 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 NAMERXN:1.2 RXNO RXNO:0000335 reductive amination A functional group modification where a carbonyl oxygen is replaced by an amine. https://orcid.org/0000-0001-5985-7429 true A reduction reaction where a nitro group is reduced to an amino group. batchelorc 2012-03-22T12:28:47Z NAMERXN:7.1 RXNO RXNO:0000337 nitro reduction to amine A reduction reaction where a nitro group is reduced to an amino group. https://orcid.org/0000-0001-5985-7429 A reduction process where an amide is transformed into an amine. batchelorc 2012-03-22T12:29:51Z NAMERXN:7.2 RXNO RXNO:0000338 amide reduction to amine A reduction process where an amide is transformed into an amine. https://orcid.org/0000-0001-5985-7429 A hydrogenation reaction where an alkene is reduced to an alkane. batchelorc 2012-03-22T12:30:40Z NAMERXN:7.6 RXNO RXNO:0000339 alkene reduction to alkane A hydrogenation reaction where an alkene is reduced to an alkane. https://orcid.org/0000-0001-5985-7429 An N-alkylation where the reactive centre is an amide nitrogen. batchelorc 2012-03-22T03:07:17Z NAMERXN:1.4 RXNO RXNO:0000340 amide N-alkylation An N-alkylation where the reactive centre is an amide nitrogen. https://orcid.org/0000-0001-5985-7429 An N-alkylation where the reactive centre is an aniline nitrogen. batchelorc 2012-03-22T03:07:44Z NAMERXN:1.5 RXNO RXNO:0000341 aniline N-alkylation An N-alkylation where the reactive centre is an aniline nitrogen. https://orcid.org/0000-0001-5985-7429 A reduction where a nitrile is replaced by an amine function. batchelorc 2012-03-22T03:12:31Z RXNO RXNO:0000342 nitrile reduction to amine A reduction where a nitrile is replaced by an amine function. https://orcid.org/0000-0001-5985-7429 A reduction reaction where an imine function is replaced by an amine. batchelorc 2012-03-22T03:13:12Z RXNO RXNO:0000343 imine reduction to amine A reduction reaction where an imine function is replaced by an amine. https://orcid.org/0000-0001-5985-7429 An alkene oxidation where the carbon-carbon double bond is cleaved. batchelorc 2012-03-22T03:15:25Z NAMERXN:1.6 RXNO RXNO:0000344 alkene oxidative cleavage An alkene oxidation where the carbon-carbon double bond is cleaved. https://orcid.org/0000-0001-5985-7429 An N-alkylation reaction where the reactive centre is an azacycle ring nitrogen. batchelorc 2012-03-22T03:22:27Z NAMERXN:1.1 RXNO RXNO:0000345 heteroaryl N-alkylation An N-alkylation reaction where the reactive centre is an azacycle ring nitrogen. https://orcid.org/0000-0001-5985-7429 A ring formation reaction where the intended product contains an oxacycle that was not in any of the reactants. batchelorc 2012-03-22T03:24:06Z NAMERXN:4.2 RXNO RXNO:0000346 oxacycle synthesis A ring formation reaction where the intended product contains an oxacycle that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 A ring formation reaction where the intended product contains an azacycle that was not in any of the reactants. batchelorc 2012-03-22T03:24:12Z NAMERXN:4.1 RXNO RXNO:0000347 azacycle synthesis A ring formation reaction where the intended product contains an azacycle that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 A ring formation reaction where the intended product contains an thiacycle that was not in any of the reactants. batchelorc 2012-03-22T03:24:23Z NAMERXN:4.3 RXNO RXNO:0000348 thiacycle synthesis A ring formation reaction where the intended product contains an thiacycle that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 A ring formation reaction where the intended product contains a heterocycle that was not in any of the reactants. batchelorc 2012-03-22T03:24:34Z NAMERXN:4 RXNO RXNO:0000349 heterocycle synthesis A ring formation reaction where the intended product contains a heterocycle that was not in any of the reactants. https://orcid.org/0000-0001-5985-7429 A hydrogenation reaction where an alkyne is reduced to an alkane. batchelorc 2012-03-22T03:30:01Z NAMERXN:7.7 RXNO RXNO:0000350 alkyne reduction to alkane A hydrogenation reaction where an alkyne is reduced to an alkane. https://orcid.org/0000-0001-5985-7429 A hydrogenation reaction where an aryl ring is reduced to a cycloalkyl ring. batchelorc 2012-03-22T03:30:50Z RXNO RXNO:0000351 aryl reduction to cycloalkyl A hydrogenation reaction where an aryl ring is reduced to a cycloalkyl ring. https://orcid.org/0000-0001-5985-7429 A hydrogenation reaction where a heteroaryl is reduced to a saturated heterocycle. batchelorc 2012-03-22T03:31:49Z RXNO RXNO:0000352 heteroaryl reduction to saturated heterocycle A hydrogenation reaction where a heteroaryl is reduced to a saturated heterocycle. https://orcid.org/0000-0001-5985-7429 An alcohol oxidation where the alcohol centre is replaced with a carboxy group. batchelorc 2012-03-22T03:34:20Z RXNO RXNO:0000353 alcohol oxidation to carboxylic acid An alcohol oxidation where the alcohol centre is replaced with a carboxy group. https://orcid.org/0000-0001-5985-7429 An oxidation reaction where a carbon centre bonded to the benzene ring is oxidized to a carboxyl group. batchelorc 2012-03-22T03:37:52Z RXNO RXNO:0000354 benzylic oxidation An oxidation reaction where a carbon centre bonded to the benzene ring is oxidized to a carboxyl group. https://orcid.org/0000-0001-5985-7429 An oxidation reaction where an allylic C-H bond is replaced by a C=O bond. batchelorc 2012-03-22T03:39:47Z RXNO RXNO:0000355 This can be done with, for instance, selenium dioxide. allylic oxidation An oxidation reaction where an allylic C-H bond is replaced by a C=O bond. http://www.chemtube3d.com/ox_se_allylic.html https://orcid.org/0000-0001-5985-7429 An oxidation reaction where an alcohol is oxidized to the corresponding carbonyl compound by a dichromate ion. batchelorc 2012-03-22T03:39:47Z RXNO RXNO:0000356 Jones oxidation An oxidation reaction where an alcohol is oxidized to the corresponding carbonyl compound by a dichromate ion. http://www.chemtube3d.com/ox_jones_oxidation.html https://orcid.org/0000-0001-5985-7429 An acylation reaction where a nitrogen atom is acylated to form an amide. batchelorc 2012-03-22T03:39:47Z NAMERXN:2.1 RXNO RXNO:0000357 N-acylation to amide An acylation reaction where a nitrogen atom is acylated to form an amide. https://orcid.org/0000-0001-5985-7429 An acylation reaction where a nitrogen atom is acylated to form a urea. batchelorc 2012-03-22T03:39:47Z NAMERXN:2.3 RXNO RXNO:0000358 N-acylation to urea An acylation reaction where a nitrogen atom is acylated to form a urea. https://orcid.org/0000-0001-5985-7429 An N-acylation reaction where a nitrogen centre is acylated to form a carbamate. batchelorc 2012-03-22T04:09:47Z NAMERXN:2.4 RXNO RXNO:0000359 N-acylation to carbamate An N-acylation reaction where a nitrogen centre is acylated to form a carbamate. https://orcid.org/0000-0001-5985-7429 An O-acylation reaction where an oxygen centre is acylated to result in an ester. batchelorc 2012-03-22T04:10:47Z NAMERXN:2.6 RXNO RXNO:0000360 O-acylation to ester An O-acylation reaction where an oxygen centre is acylated to result in an ester. https://orcid.org/0000-0001-5985-7429 A functional group modification where a nitrile reacts with an alcohol under acid catalysis to form an amidine or ester. RXNO RXNO:0000361 Pinner reaction A functional group modification where a nitrile reacts with an alcohol under acid catalysis to form an amidine or ester. https://orcid.org/0000-0001-5985-7429 An oxidation reaction where a nitrile reacts with an alcohol to form an alkyl imidate. RXNO RXNO:0000362 nitrile alcoholysis An oxidation reaction where a nitrile reacts with an alcohol to form an alkyl imidate. https://orcid.org/0000-0001-5985-7429 A functional group modification where an amide is converted to an imidoyl chloride. batchelorc 2012-03-22T05:04:20Z NAMERXN:9.2 RXNO RXNO:0000363 amide to imidoyl chloride conversion A functional group modification where an amide is converted to an imidoyl chloride. https://orcid.org/0000-0001-5985-7429 A functional group modification where an alcohol is converted to a halide. batchelorc 2012-03-22T05:05:15Z NAMERXN:9.1 RXNO RXNO:0000364 alcohol to halide conversion A functional group modification where an alcohol is converted to a halide. https://orcid.org/0000-0001-5985-7429 A functional group modification where a carboxylic acid is converted to an acid chloride. batchelorc 2012-03-22T05:06:09Z NAMERXN:9.3 RXNO RXNO:0000365 carboxylic acid to acid chloride conversion A functional group modification where a carboxylic acid is converted to an acid chloride. https://orcid.org/0000-0001-5985-7429 A functional group modification where a nitrile is transformed into a carboxylic acid. batchelorc 2012-03-22T05:12:32Z NAMERXN:9.4 RXNO RXNO:0000366 nitrile to acid conversion A functional group modification where a nitrile is transformed into a carboxylic acid. https://orcid.org/0000-0001-5985-7429 A functional group modification where a carbonyl compound is converted to an imine. batchelorc 2012-03-22T05:17:03Z NAMERXN:9.6 RXNO RXNO:0000367 carbonyl compound to imine conversion A functional group modification where a carbonyl compound is converted to an imine. https://orcid.org/0000-0001-5985-7429 Oxidation of an alkene to an allene by heating with formaldehyde, an amine and an inorganic salt. batchelorc 2014-01-08T13:48:00Z Crabbe homologation RXNO RXNO:0000368 Crabbé homologation Oxidation of an alkene to an allene by heating with formaldehyde, an amine and an inorganic salt. doi:10.1039/c39790000859 https://orcid.org/0000-0001-5985-7429 A carbon-carbon coupling reaction between an arene and a carbonyl compound (an acylation) or an alkyl compound that can form a carbocation (an alkylation) to form a substituted arene. NAMERXN:3.10 RXNO RXNO:0000369 Friedel-Crafts reaction A carbon-carbon coupling reaction between an arene and a carbonyl compound (an acylation) or an alkyl compound that can form a carbocation (an alkylation) to form a substituted arene. https://orcid.org/0000-0001-5985-7429 A functional group modification of a nitrile to a 1H-tetrazole by addition of sodium azide. RXNO RXNO:0000370 Demko-Sharpless reaction A functional group modification of a nitrile to a 1H-tetrazole by addition of sodium azide. doi:10.1021/jo010635w https://orcid.org/0000-0001-5985-7429 A diazotisation that proceeds by the addition of nitrous acid, nitric acid and water, resulting in a diazonium nitrate salt. https://www.rsc.org/Merck-Index/reaction/r174/ RXNO RXNO:0000371 Griess reaction A diazotisation that proceeds by the addition of nitrous acid, nitric acid and water, resulting in a diazonium nitrate salt. https://orcid.org/0000-0001-5985-7429 An N-arylation reaction where the reactive centre is an azacycle ring nitrogen. NAMERXN:1.3 RXNO RXNO:0000372 heteroaryl N-arylation An N-arylation reaction where the reactive centre is an azacycle ring nitrogen. https://orcid.org/0000-0001-5985-7429 A planned reaction step in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged. NAMERXN:10 RXNO RXNO:0000373 this is not part of David's grand diagram - well spotted Roger functional group addition step A planned reaction step in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged. https://orcid.org/0000-0001-5985-7429 Arylation of an amine or an alcohol with an arylboronic acid, stannane or siloxane in air with a copper acetate catalyst. Chan-Lam reaction Chan-Lam-Evans coupling Chan-Lam-Evans reaction RXNO RXNO:0000374 The canonical variant is the N-arylation of an amine with an arylboronic acid. Chan-Lam coupling Arylation of an amine or an alcohol with an arylboronic acid, stannane or siloxane in air with a copper acetate catalyst. doi:10.1016/j.tet.2012.06.015 true N-methylation of a primary or secondary amine with formic acid and formaldehyde to yield a tertiary amine. Eschweiler-Clarke reaction RXNO RXNO:0000376 Eschweiler-Clarke methylation N-methylation of a primary or secondary amine with formic acid and formaldehyde to yield a tertiary amine. https://orcid.org/0000-0001-5985-7429 Coupling of two aromatic rings in the presence of a Lewis acid catalyst. https://www.rsc.org/Merck-Index/reaction/r390/ RXNO RXNO:0000377 Scholl reaction Coupling of two aromatic rings in the presence of a Lewis acid catalyst. https://orcid.org/0000-0001-5985-7429 Scholl reaction within a single molecule to form a larger ring system. RXNO RXNO:0000378 intramolecular Scholl reaction Scholl reaction within a single molecule to form a larger ring system. https://orcid.org/0000-0001-5985-7429 Scholl reaction between two aromatic molecules to form a single molecule. RXNO RXNO:0000379 intermolecular Scholl reaction Scholl reaction between two aromatic molecules to form a single molecule. https://orcid.org/0000-0001-5985-7429 Reaction of a cyclohexanone with methyl vinyl ketone to form a fused-ring cyclohexenone. It is a Michael reaction followed by an intramolecular aldol condensation. https://www.rsc.org/Merck-Index/reaction/r373/ RXNO RXNO:0000380 Robinson annulation Reaction of a cyclohexanone with methyl vinyl ketone to form a fused-ring cyclohexenone. It is a Michael reaction followed by an intramolecular aldol condensation. https://orcid.org/0000-0001-5985-7429 Rearrangement of a beta-amino alcohol to yield a carbonyl compound. In the first step the amine is diazotised by reaction with nitrous acid. https://www.rsc.org/Merck-Index/reaction/r432/ RXNO RXNO:0000381 Tiffeneau-Demjanov rearrangement Rearrangement of a beta-amino alcohol to yield a carbonyl compound. In the first step the amine is diazotised by reaction with nitrous acid. https://orcid.org/0000-0001-5985-7429 Substitution reaction of a primary amine via deazotisation to yield a mixture of the corresponding primary alcohol and secondary alcohol. https://www.rsc.org/Merck-Index/reaction/r106/ RXNO RXNO:0000382 TODO: Not *entirely* sure how we classify this. Have given it multiple parentage for the now. Demjanov rearrangement Substitution reaction of a primary amine via deazotisation to yield a mixture of the corresponding primary alcohol and secondary alcohol. https://orcid.org/0000-0001-5985-7429 Base-catalysed rearrangement of a cyclic alpha-haloketone to the ring-contracted cyclic carboxylic acid. RXNO RXNO:0000384 cyclic alpha-haloketone Favorskii rearrangement Base-catalysed rearrangement of a cyclic alpha-haloketone to the ring-contracted cyclic carboxylic acid. https://orcid.org/0000-0001-5985-7429 Base-catalysed rearrangement of an alpha-haloketone to a carboxylic acid or ester or amide. RXNO RXNO:0000385 Favorskii rearrangement Base-catalysed rearrangement of an alpha-haloketone to a carboxylic acid or ester or amide. https://orcid.org/0000-0001-5985-7429 Favorskii rearrangement of a cyclic alpha-dibromoketone followed by decarboxylation to yield a ring-contracted cyclic ketone. RXNO RXNO:0000386 Wallach degradation Favorskii rearrangement of a cyclic alpha-dibromoketone followed by decarboxylation to yield a ring-contracted cyclic ketone. https://orcid.org/0000-0001-5985-7429 Reaction of a carbonyl compound with a dimethyl diazomethyl phosphonate under basic conditions to yield an alkyne. https://www.rsc.org/Merck-Index/reaction/r395/ RXNO RXNO:0000387 Seyferth-Gilbert homologation Reaction of a carbonyl compound with a dimethyl diazomethyl phosphonate under basic conditions to yield an alkyne. https://orcid.org/0000-0001-5985-7429 Reaction of an aldehyde with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne. RXNO RXNO:0000388 Seyferth-Gilbert aldehyde homologation Reaction of an aldehyde with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne. https://orcid.org/0000-0001-5985-7429 Reaction of a ketone with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne. RXNO RXNO:0000389 Seyferth-Gilbert ketone homologation Reaction of a ketone with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne. https://orcid.org/0000-0001-5985-7429 Seyferth-Gilbert aldehyde homologation where the Seyferth-Gilbert reagent is generated in situ by reaction with methanol and potassium carbonate. https://www.rsc.org/Merck-Index/reaction/r395/ Bestmann modification Ohira-Bestmann homologation Ohira-Bestmann modification RXNO RXNO:0000390 Seyferth-Gilbert-Bestmann homologation Seyferth-Gilbert aldehyde homologation where the Seyferth-Gilbert reagent is generated in situ by reaction with methanol and potassium carbonate. https://orcid.org/0000-0001-5985-7429 Synthesis of a pyrazole by condensation of a 1,3-dicarbonyl compound with a hydrazine, hydrazide, semicarbazide or aminoguanidine. https://www.rsc.org/Merck-Index/reaction/r233/ RXNO RXNO:0000391 Knorr pyrazole synthesis Synthesis of a pyrazole by condensation of a 1,3-dicarbonyl compound with a hydrazine, hydrazide, semicarbazide or aminoguanidine. https://orcid.org/0000-0001-5985-7429 A reaction in which the intended product is a pyrazole that was not present in any of the reactants. RXNO RXNO:0000392 pyrazole synthesis A reaction in which the intended product is a pyrazole that was not present in any of the reactants. https://orcid.org/0000-0001-5985-7429 A reaction in which the intended product is a quinoline that was not present in any of the reactants. RXNO RXNO:0000393 quinoline synthesis A reaction in which the intended product is a quinoline that was not present in any of the reactants. https://orcid.org/0000-0001-5985-7429 Synthesis of an alpha-hydroxyquinoline by reaction of a beta-ketoester and an arylamine then dehydration with concentrated sulfuric acid. https://www.rsc.org/Merck-Index/reaction/r234/ RXNO RXNO:0000394 Knorr quinoline synthesis Synthesis of an alpha-hydroxyquinoline by reaction of a beta-ketoester and an arylamine then dehydration with concentrated sulfuric acid. https://orcid.org/0000-0001-5985-7429 A reaction in which the intended product is an indole that was not present in any of the reactants. RXNO RXNO:0000395 indole synthesis A reaction in which the intended product is an indole that was not present in any of the reactants. https://orcid.org/0000-0001-5985-7429 Palladium-catalysed synthesis of a 2,3-substituted indole by reaction of an ortho-iodoaniline with an internal alkyne. https://www.rsc.org/Merck-Index/reaction/r250/ Larock indolisation Larock indolization RXNO RXNO:0000396 Larock indole synthesis Palladium-catalysed synthesis of a 2,3-substituted indole by reaction of an ortho-iodoaniline with an internal alkyne. https://orcid.org/0000-0001-5985-7429 Reaction of an organic diazo compound with an acetylene to yield a pyrazole. https://www.rsc.org/Merck-Index/reaction/r323/ RXNO RXNO:0000397 Pechmann pyrazole synthesis Reaction of an organic diazo compound with an acetylene to yield a pyrazole. https://orcid.org/0000-0001-5985-7429 A reaction in which the intended product is a benzimidazole that was not present in any of the reactants. RXNO RXNO:0000398 benzimidazole synthesis A reaction in which the intended product is a benzimidazole that was not present in any of the reactants.