The formation of the 2-bicyclo[3.1.0]hexyl cation by deamination and solvolysis, and the effect of methyl substitution at C-5

Abstract

Deamination of endo- and exo-2-aminobicyclo[3.1.0]hexanes (7) and (8) and solvolysis of the corresponding 2-chloro-compounds (1) and (2) yield very similar ratios of products showing the intervention of a common 2-cation. Rate studies of solvolysis of 2-substituted bicyclohexyl derivatives and some 5-methyl-substituted compounds indicate that the normal rate-enhancing effect of the cyclopropyl group is due to delocalisation of the symmetrical homoallyl type for endo- and exo-leaving groups. Deuterium scrambling from the 5-position was not observed in solvolysis of chlorides (1) and (2).