Eschenmoser–Tanabe fragmentation
E398760
The Eschenmoser–Tanabe fragmentation is an organic reaction that cleaves certain α,β-epoxy ketones or related substrates to form carbonyl compounds via a synthetically useful carbon–carbon bond fragmentation.
All labels observed (2)
| Label | Occurrences |
|---|---|
| Eschenmoser–Tanabe fragmentation canonical | 2 |
| Eschenmoser fragmentation | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T3935408 — 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–Tanabe fragmentation Context triple: [Albert Eschenmoser, knownFor, Eschenmoser–Tanabe fragmentation]
-
A.
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.
-
B.
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.
-
C.
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.
-
D.
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.
-
E.
Woodward–Hoffmann rules
The Woodward–Hoffmann rules are fundamental principles in organic chemistry that predict the stereochemistry and feasibility of pericyclic reactions based on orbital symmetry considerations.
- 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–Tanabe fragmentation Target entity description: The Eschenmoser–Tanabe fragmentation is an organic reaction that cleaves certain α,β-epoxy ketones or related substrates to form carbonyl compounds via a synthetically useful carbon–carbon bond fragmentation.
-
A.
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.
-
B.
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.
-
C.
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.
-
D.
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.
-
E.
Woodward–Hoffmann rules
The Woodward–Hoffmann rules are fundamental principles in organic chemistry that predict the stereochemistry and feasibility of pericyclic reactions based on orbital symmetry considerations.
- F. None of above. chosen
Statements (32)
| Predicate | Object |
|---|---|
| instanceOf |
named reaction
ⓘ
organic reaction ⓘ |
| category |
carbonyl chemistry
ⓘ
epoxide chemistry ⓘ |
| drivingForce |
formation of stable carbonyl products
ⓘ
relief of epoxide ring strain ⓘ |
| field | organic chemistry ⓘ |
| keyStep | carbon–carbon bond fragmentation ⓘ |
| mechanisticFeature |
base-promoted ring opening of epoxide
ⓘ
formation of an enolate intermediate ⓘ β-elimination ⓘ |
| namedAfter |
Albert Eschenmoser
ⓘ
Kazuo Tanabe ⓘ |
| notableFeature |
converts epoxyketones into shorter-chain carbonyl compounds
ⓘ
useful in complex molecule degradation studies ⓘ |
| reactionType |
carbon–carbon bond cleavage
ⓘ
fragmentation reaction ⓘ |
| relatedTo |
Eschenmoser fragmentation
ⓘ
linked to:
Eschenmoser–Tanabe fragmentation
Grob fragmentation ⓘ |
| selectivity | regioselective C–C bond cleavage ⓘ |
| substrateRequirement | α,β-epoxy carbonyl system ⓘ |
| syntheticUse |
carbon skeleton rearrangement
ⓘ
cleavage of complex molecules ⓘ generation of aldehydes ⓘ generation of ketones ⓘ |
| transforms |
related α,β-epoxy carbonyl substrates
ⓘ
α,β-epoxy ketones ⓘ |
| typicalConditions |
basic conditions
ⓘ
nucleophilic reagents ⓘ |
| usedFor | strategic C–C bond disconnection ⓘ |
| usedIn | synthetic organic chemistry ⓘ |
| yields | carbonyl compounds ⓘ |
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–Tanabe fragmentation Description of subject: The Eschenmoser–Tanabe fragmentation is an organic reaction that cleaves certain α,β-epoxy ketones or related substrates to form carbonyl compounds via a synthetically useful carbon–carbon bond fragmentation.
Referenced by (3)
Full triples — surface form annotated when it differs from this entity's canonical label.