Mechanism of the directing influence of functional groups and the geometry of reactant molecules on peroxide epoxidation of alkenes

Abstract

The influence of steric and electronic factors on the reactivity and the stereochemical outcome of epoxidation of cycloalkenes and prochiral alkenes by alkyl hydroperoxides, peroxy acids, oxaziridines, dioxiranes and dimethyl-α-peroxy lactone is analysed comparatively and generalised. The distinctive features of the directing influence of functional groups on the stereochemistry of the epoxide ring closure in the series of ionic, radical and molecular reactions are demonstrated. Some variants alternative to known reaction mechanisms are proposed. The bibliography includes 114 references.