Stork–Danheiser rearrangement
E683998
The Stork–Danheiser rearrangement is an organic reaction that transforms certain allylic alcohol derivatives into rearranged carbonyl compounds via a sigmatropic shift, widely used in complex molecule synthesis.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Stork–Danheiser rearrangement canonical | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T7731594 — 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: Stork–Danheiser rearrangement Context triple: [Gilbert Stork, knownFor, Stork–Danheiser rearrangement]
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A.
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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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.
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C.
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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D.
Robinson annulation reaction
The Robinson annulation reaction is a classic organic chemistry transformation that forms six-membered rings by combining a Michael addition with an intramolecular aldol condensation, widely used in the synthesis of complex cyclic molecules and natural products.
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E.
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.
- 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: Stork–Danheiser rearrangement Target entity description: The Stork–Danheiser rearrangement is an organic reaction that transforms certain allylic alcohol derivatives into rearranged carbonyl compounds via a sigmatropic shift, widely used in complex molecule synthesis.
-
A.
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.
-
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.
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.
-
D.
Robinson annulation reaction
The Robinson annulation reaction is a classic organic chemistry transformation that forms six-membered rings by combining a Michael addition with an intramolecular aldol condensation, widely used in the synthesis of complex cyclic molecules and natural products.
-
E.
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.
- F. None of above. chosen
Statements (43)
| Predicate | Object |
|---|---|
| instanceOf |
named reaction
ⓘ
organic reaction ⓘ rearrangement reaction ⓘ |
| application |
construction of quaternary carbon centers
ⓘ
synthesis of polycyclic frameworks ⓘ |
| bondChange |
C–C bond migration
ⓘ
formation of carbonyl group ⓘ |
| category |
carbon–carbon bond-forming reaction
ⓘ
pericyclic reaction ⓘ |
| drivingForce | formation of conjugated carbonyl system ⓘ |
| field | organic chemistry ⓘ |
| governedBy | orbital symmetry rules ⓘ |
| importance |
enables strategic skeletal reorganization
ⓘ
valuable for late-stage functionalization ⓘ |
| involvesIntermediate |
allylic cation-like transition state
ⓘ
enone intermediate ⓘ |
| keyStep | [3,3]-sigmatropic rearrangement ⓘ |
| levelOfUse | widely used in complex synthesis ⓘ |
| mechanismFeature | sigmatropic shift ⓘ |
| namedAfter |
Gilbert Stork
NERFINISHED
ⓘ
Robert L. Danheiser NERFINISHED ⓘ |
| operatesThrough | concerted pericyclic transition state ⓘ |
| productClass |
aldehydes
ⓘ
ketones ⓘ |
| productType | rearranged carbonyl compounds ⓘ |
| reactionClass | allylic to carbonyl rearrangement ⓘ |
| reactionType |
allylic rearrangement
ⓘ
sigmatropic rearrangement ⓘ |
| relatedTo |
Claisen rearrangement
NERFINISHED
ⓘ
Eschenmoser–Claisen rearrangement NERFINISHED ⓘ Ireland–Claisen rearrangement NERFINISHED ⓘ |
| selectivity |
regioselective
ⓘ
stereoselective ⓘ |
| substrateClass | allylic alcohols ⓘ |
| substrateClass | allylic esters ⓘ |
| substrateClass | allylic ethers ⓘ |
| transforms | allylic alcohol derivatives ⓘ |
| typicalContext | multistep synthetic sequences ⓘ |
| typicalOutcome | migration of substituent along allylic system ⓘ |
| usedBy | synthetic organic chemists ⓘ |
| usedIn |
complex molecule synthesis
ⓘ
natural product synthesis ⓘ total 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: Stork–Danheiser rearrangement Description of subject: The Stork–Danheiser rearrangement is an organic reaction that transforms certain allylic alcohol derivatives into rearranged carbonyl compounds via a sigmatropic shift, widely used in complex molecule synthesis.
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.