Diels–Alder reaction
E701868
The Diels–Alder reaction is a fundamental organic chemistry cycloaddition that forms six-membered rings by combining a conjugated diene with a dienophile in a single, stereospecific step.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Diels–Alder reaction canonical | 7 |
How this entity was disambiguated
This entity first appeared as the object of triple T7953326 — 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: Diels–Alder reaction Context triple: [Otto Diels, knownFor, Diels–Alder reaction]
-
A.
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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B.
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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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.
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.
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.
- 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: Diels–Alder reaction Target entity description: The Diels–Alder reaction is a fundamental organic chemistry cycloaddition that forms six-membered rings by combining a conjugated diene with a dienophile in a single, stereospecific step.
-
A.
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.
-
B.
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.
-
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.
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.
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.
- F. None of above. chosen
Statements (50)
| Predicate | Object |
|---|---|
| instanceOf |
cycloaddition reaction
ⓘ
organic reaction ⓘ pericyclic reaction ⓘ |
| bondBreaking | two pi bonds ⓘ |
| bondFormation | two new sigma bonds ⓘ |
| canBe |
asymmetric
ⓘ
intermolecular ⓘ intramolecular ⓘ |
| catalyzedBy |
Brønsted acids
ⓘ
Lewis acids ⓘ
linked to:
Lewis superacids
organocatalysts ⓘ transition metal complexes ⓘ |
| doesNotRequire | photochemical activation ⓘ |
| drivingForce | formation of sigma bonds from pi bonds ⓘ |
| electronDemand |
inverse electron-demand
ⓘ
normal electron-demand ⓘ |
| endoPreference | secondary orbital interactions ⓘ |
| formsRingSize | six-membered ring ⓘ |
| hasVariant |
asymmetric Diels–Alder reaction
ⓘ
hetero-Diels–Alder reaction ⓘ intramolecular Diels–Alder reaction ⓘ inverse electron-demand Diels–Alder reaction ⓘ |
| isReversibleAt | high temperature ⓘ |
| mechanism | concerted ⓘ |
| namedAfter |
Kurt Alder
ⓘ
Otto Diels ⓘ |
| obeys | Woodward–Hoffmann rules ⓘ |
| orbitalInteraction |
HOMO(diene)–LUMO(dienophile)
ⓘ
HOMO(dienophile)–LUMO(diene) ⓘ |
| reactant |
conjugated diene
ⓘ
dienophile ⓘ |
| reactionType | [4+2] cycloaddition ⓘ |
| recognizedBy |
Nobel Prize in Chemistry 1950 to Diels and Alder
ⓘ
linked to:
Nobel Prize in Chemistry 1950
|
| regioselectivity |
influenced by substituent electronic effects
ⓘ
predictable by frontier molecular orbital theory ⓘ |
| requires |
s-cis conformation of diene
ⓘ
thermal activation ⓘ |
| reverseReaction | retro-Diels–Alder reaction ⓘ |
| stereochemicalFeature |
suprafacial on diene
ⓘ
suprafacial on dienophile ⓘ |
| stereochemistry | stereospecific ⓘ |
| stereoselectivity | endo rule ⓘ |
| thermodynamics | generally exothermic ⓘ |
| tolerates | a wide range of functional groups ⓘ |
| usedFor |
construction of carbocyclic rings
ⓘ
construction of heterocyclic rings ⓘ |
| usedIn |
natural product synthesis
ⓘ
pharmaceutical synthesis ⓘ polymer chemistry ⓘ |
| yearProposed | 1928 ⓘ |
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: Diels–Alder reaction Description of subject: The Diels–Alder reaction is a fundamental organic chemistry cycloaddition that forms six-membered rings by combining a conjugated diene with a dienophile in a single, stereospecific step.
Referenced by (7)
Full triples — surface form annotated when it differs from this entity's canonical label.