The rearrangement was first discovered in bicyclic terpenes for example the conversion of isoborneol to camphene ref8:
In a simple demonstration reaction of 1,4-dimethoxybenzene with either 2-methyl-2-butanol or 3-methyl-2-butanol in sulfuric acid and acetic acid yields the same disubstituted product,ref 10 the latter via a hydride shift of the cationic intermediate:
Plausible mechanisms of the Wagner-Meerwein rearrangement of diepoxyisoindoles:
The related Nametkin rearrangement named after sergey nametkin involves the rearrangement of methyl groups in certain terpenes. In some cases the reaction type is also called a retropinacol rearrangement
- Wagner, G.
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