Retropinacol rearrangement

Wagner-Meerwein rearrangement

A Wagner-Meerwein rearrangement is a class of carbocation 1,2-rearrangement reactions in which a hydrogen, alkyl or aryl group migrates from one carbon to a neighboring carbon.

Several reviews have been published.

The rearrangement was first discovered in bicyclic terpenes for example the conversion of isoborneol to camphene :

The related Nametkin rearrangement named after Sergey Namyotkin involves the rearrangement of methyl groups in certain terpenes. In some cases the reaction type is also called a retropinacol rearrangement (see Pinacol rearrangement).

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