Corey–Chaykovsky reagent
E466670
The Corey–Chaykovsky reagent is an organosulfur ylide reagent widely used in organic synthesis to convert carbonyl compounds into epoxides and aziridines.
All labels observed (2)
| Label | Occurrences |
|---|---|
| Corey–Chaykovsky reagent canonical | 1 |
| Liotta reagent | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T4741220 — resolving that mention is where its identity was fixed. The disambiguator weighed these candidate entities and picked the highlighted one (or “None”, minting a new entity). This is how homonymy is resolved: the same surface form can point to different entities.
NED1
Entity disambiguation (via context triple)
gpt-5-mini-2025-08-07
Target entity: Corey–Chaykovsky reagent Context triple: [E. J. Corey, developedReagent, Corey–Chaykovsky reagent]
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A.
Eschenmoser
Eschenmoser is a Swiss surname most notably associated with Albert Eschenmoser, a prominent organic chemist known for his pioneering work in the synthesis of complex natural products and studies on the origin of life.
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B.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
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C.
Barton reaction
The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.
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D.
Eschenmoser–Claisen rearrangement
The Eschenmoser–Claisen rearrangement is a variant of the Claisen rearrangement in organic chemistry that converts allylic alcohols and amides into γ,δ-unsaturated carbonyl compounds via a [3,3]-sigmatropic rearrangement.
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E.
Buchwald–Hartwig amination
The Buchwald–Hartwig amination is a palladium-catalyzed cross-coupling reaction that forms carbon–nitrogen bonds by coupling aryl (or vinyl) halides with amines, widely used in the synthesis of pharmaceuticals and fine chemicals.
- F. None of above. chosen
- G. Unsure - the case is ambiguous/there is not enough information to decide.
NED2
Entity disambiguation (via description)
gpt-5-mini-2025-08-07
Target entity: Corey–Chaykovsky reagent Target entity description: The Corey–Chaykovsky reagent is an organosulfur ylide reagent widely used in organic synthesis to convert carbonyl compounds into epoxides and aziridines.
-
A.
Eschenmoser
Eschenmoser is a Swiss surname most notably associated with Albert Eschenmoser, a prominent organic chemist known for his pioneering work in the synthesis of complex natural products and studies on the origin of life.
-
B.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
-
C.
Barton reaction
The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.
-
D.
Eschenmoser–Claisen rearrangement
The Eschenmoser–Claisen rearrangement is a variant of the Claisen rearrangement in organic chemistry that converts allylic alcohols and amides into γ,δ-unsaturated carbonyl compounds via a [3,3]-sigmatropic rearrangement.
-
E.
Buchwald–Hartwig amination
The Buchwald–Hartwig amination is a palladium-catalyzed cross-coupling reaction that forms carbon–nitrogen bonds by coupling aryl (or vinyl) halides with amines, widely used in the synthesis of pharmaceuticals and fine chemicals.
- F. None of above. chosen
Statements (48)
| Predicate | Object |
|---|---|
| instanceOf |
named reaction reagent
ⓘ
organosulfur compound ⓘ synthetic reagent ⓘ ylide reagent ⓘ |
| advantages |
high stereocontrol
ⓘ
mild reaction conditions ⓘ operational simplicity ⓘ |
| baseUsedWith |
potassium tert-butoxide
ⓘ
sodium hydride ⓘ |
| category |
aziridination reagents
ⓘ
epoxidation reagents ⓘ organosulfur ylides ⓘ |
| developedBy |
Elias James Corey
NERFINISHED
ⓘ
Michael Chaykovsky NERFINISHED ⓘ |
| discoveredIn | 1960s ⓘ |
| field | organic chemistry ⓘ |
| hasComponent |
sulfonium ylide
ⓘ
sulfoxonium ylide ⓘ |
| mechanismFeature |
betainic intermediate formation
ⓘ
intramolecular SN2 ring closure ⓘ |
| namedAfter |
Elias James Corey
NERFINISHED
ⓘ
Michael Chaykovsky NERFINISHED ⓘ |
| produces |
aziridines
ⓘ
epoxides ⓘ |
| reactionType |
1,2-addition to C=O bond
ⓘ
nucleophilic addition to carbonyl group ⓘ ring-forming reaction ⓘ |
| relatedReaction |
Corey–Chaykovsky aziridination
NERFINISHED
ⓘ
Corey–Chaykovsky epoxidation NERFINISHED ⓘ |
| relatedTo |
Wittig reagent
ⓘ
sulfonium ylides ⓘ sulfoxonium ylides ⓘ |
| selectivity |
chemoselective for carbonyl groups
ⓘ
tolerant of many functional groups ⓘ |
| solvent |
dimethyl sulfoxide
ⓘ
polar aprotic solvents ⓘ |
| stereochemicalOutcome |
retention of configuration at carbonyl carbon
ⓘ
stereospecific epoxide formation ⓘ |
| typicalForm |
dimethyloxosulfonium methylide
ⓘ
trimethylsulfonium iodide-derived ylide ⓘ |
| usedFor |
aziridination of imines
ⓘ
conversion of aldehydes to epoxides ⓘ conversion of imines to aziridines ⓘ conversion of ketones to epoxides ⓘ epoxidation of carbonyl compounds ⓘ |
| usedIn |
medicinal chemistry
ⓘ
natural product synthesis ⓘ stereoselective synthesis ⓘ |
How these facts were elicited
The pipeline generated the facts above by prompting gpt-5.1 with this entity's name + description and the instruction below.
Instruction
You are a knowledge base construction expert. Given a subject entity and a description of it, return factual statements that you know for the subject as a JSON list of dictionaries(triples), where keys must be "subject", "predicate" and "object". The number of facts may be very high, between 25 to 50 or more, for very popular subjects. For less popular subjects, the number of facts can be very low, like 5 or 10. # Requirements - If you don't know the subject at all, return an empty list. - If the subject is not a named entity, return an empty list. - Include at least one triple where predicate is "instanceOf". - Do not get too wordy. - Separate several objects into multiple triples with one object.
Input
Subject: Corey–Chaykovsky reagent Description of subject: The Corey–Chaykovsky reagent is an organosulfur ylide reagent widely used in organic synthesis to convert carbonyl compounds into epoxides and aziridines.
Referenced by (2)
Full triples — surface form annotated when it differs from this entity's canonical label.