[3,3]-Sigmatropic rearrangement

Claisen rearangement on an aromatic system

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Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

The first step in the reaction is a pericyclic [3,3]-sigmatropic rearrangement, which happens through a chair-like transition state. The second step is a simple proton transfer to regenerate aromaticity.