Octet / Reactions
Cope Rearrangement
Cope Rearrangement (Pericyclic.) Converts C=CCC=CC to CC=CCC=C using Heat. Conditions: Thermal (150-200°C). Stereochemistry: Chair-like transition state preferred.
Pericyclic
Reaction details
Name
Cope Rearrangement
Type
Pericyclic
Starting Material
C=CCC=CC
Product
CC=CCC=C
Reagents
Heat
Conditions
Thermal (150-200°C)
Mechanism
- Smiles
C=CCC=CC
- Description
1,5-Hexadiene
- Smiles
CC=CCC=C
- Description
[3,3]-Sigmatropic rearrangement
Stereochemistry
Chair-like transition state preferred
Tips
[3,3]-Sigmatropic rearrangement
No intermediates - concerted
Oxy-Cope: 3-hydroxy-1,5-diene → unsaturated carbonyl
Claisen is the O-analog
Related Reactions
claisen-rearrangement
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