Wagner–Meerwein rearrangement

As such, a Wagner–Meerwein shift is a thermally allowed pericyclic process with the Woodward-Hoffmann symbol [ω0s + σ2s].

The reaction is named after the Russian chemist Yegor Yegorovich Vagner; he had German origin and published in German journals as Georg Wagner; and Hans Meerwein.

[3][4][5][6][7] The rearrangement was first discovered in bicyclic terpenes for example the conversion of isoborneol to camphene:[8] The story of the rearrangement reveals that many scientists were puzzled with this and related reactions and its close relationship to the discovery of carbocations as intermediates.

[9] 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,[10] the latter via a hydride shift of the cationic intermediate: Currently, there are works relating to the use of skeletal rearrangement in the synthesis of bridged azaheterocycles.

These data are summarized in [11] Plausible mechanisms of the Wagner–Meerwein rearrangement of diepoxyisoindoles: