Eschenmoser sulfide contraction
E398761
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.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Eschenmoser sulfide contraction canonical | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T3935409 — 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: Eschenmoser sulfide contraction Context triple: [Albert Eschenmoser, knownFor, Eschenmoser sulfide contraction]
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A.
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.
-
B.
Barton–McCombie deoxygenation
Barton–McCombie deoxygenation is an organic chemistry reaction that converts alcohols into the corresponding hydrocarbons via radical-mediated removal of the hydroxyl group.
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C.
Suzuki coupling
Suzuki coupling is a widely used palladium-catalyzed cross-coupling reaction that forms carbon–carbon bonds between organoboron compounds and organic halides, fundamental in organic synthesis and pharmaceutical chemistry.
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D.
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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E.
Sharpless epoxidation
Sharpless epoxidation is a landmark asymmetric oxidation reaction in organic chemistry that enables the enantioselective conversion of allylic alcohols to epoxides using chiral catalysts.
- 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: Eschenmoser sulfide contraction Target entity description: 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.
-
A.
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.
-
B.
Barton–McCombie deoxygenation
Barton–McCombie deoxygenation is an organic chemistry reaction that converts alcohols into the corresponding hydrocarbons via radical-mediated removal of the hydroxyl group.
-
C.
Suzuki coupling
Suzuki coupling is a widely used palladium-catalyzed cross-coupling reaction that forms carbon–carbon bonds between organoboron compounds and organic halides, fundamental in organic synthesis and pharmaceutical chemistry.
-
D.
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.
-
E.
Sharpless epoxidation
Sharpless epoxidation is a landmark asymmetric oxidation reaction in organic chemistry that enables the enantioselective conversion of allylic alcohols to epoxides using chiral catalysts.
- F. None of above. chosen
Statements (40)
| Predicate | Object |
|---|---|
| instanceOf |
named reaction
ⓘ
organic reaction ⓘ rearrangement reaction ⓘ |
| category |
carbonyl-forming reactions
ⓘ
named organic reactions ⓘ sulfur chemistry ⓘ |
| commonUse |
construction of amide carbonyls
ⓘ
construction of ester carbonyls ⓘ |
| developedBy | Albert Eschenmoser ⓘ |
| field | organic chemistry ⓘ |
| hasKeyStep |
loss of sulfur-containing fragment
ⓘ
rearrangement of sulfur-stabilized intermediate ⓘ |
| hasProduct |
amide
ⓘ
carbonyl compound ⓘ ester ⓘ |
| hasReactant | sulfur-containing intermediate ⓘ |
| involvesBondChange |
C–C bond cleavage
ⓘ
C–C bond formation ⓘ C–S bond cleavage ⓘ |
| involvesElement | sulfur ⓘ |
| mechanismFeature |
C–C bond contraction
ⓘ
rearrangement of sulfur-containing intermediates ⓘ sulfur extrusion ⓘ |
| namedAfter | Albert Eschenmoser ⓘ |
| reactionClass | heteroatom-assisted rearrangement ⓘ |
| reactionType |
contraction
ⓘ
rearrangement ⓘ |
| relatedTo |
Eschenmoser–Claisen rearrangement
ⓘ
sulfur extrusion reactions ⓘ |
| transformsFunctionalGroup |
thioacetal to carbonyl
ⓘ
thioamide to carbonyl derivative ⓘ |
| typicalSubstrate |
sulfur-containing acetal-like intermediate
ⓘ
sulfur-containing aminal-like intermediate ⓘ |
| usedFor |
backbone editing in complex molecules
ⓘ
ring-contraction transformations ⓘ |
| usedIn |
complex molecule synthesis
ⓘ
natural product synthesis ⓘ total synthesis ⓘ |
| usesIntermediate |
thioamide
ⓘ
thiol ester ⓘ |
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: Eschenmoser sulfide contraction Description of subject: 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.
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.