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.
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 NERFINISHED ⓘ 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
NERFINISHED
ⓘ
Otto Diels NERFINISHED ⓘ |
| obeys | Woodward–Hoffmann rules NERFINISHED ⓘ |
| 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 NERFINISHED ⓘ |
| 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 ⓘ |
Referenced by (3)
Full triples — surface form annotated when it differs from this entity's canonical label.