Claisen rearrangement on an aromatic system – [3,3]-Sigmatropic rearrangement

ThionylChloride

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

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.

K. C. Majumdar and R. K. Nandi, Tetrahedron, 2013, 69, 6921–6957.

 

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