Search

A comparative study was conducted to investigate the reactivity of primary and quaternary allylic and homoallylic alkenylammonium salts with dimethyldioxirane and m-chloroperbenzoic acid. The study determined the stereochemical outcome of the epoxidation of the cyclic quaternary allylic salt (2-cyclohexenyl)trimethylammonium p-chlorobenzenesulfonate with dimethyldioxirane and m-chloroperbenzoic acid. It also determined the epoxidation rate constants for the reaction of select allylic and homoallylic primary and quaternary ammonium salts.

The protonation of epoxy compounds with arenesulfonic acids is a suitable procedure for synthesizing epoxyalkylamines and protecting primary and secondary alkenylamines from N-oxidation by electrophilic epoxidation. Dimethyldioxirane, m-CPBA and methyl(trifluoromethyl) dioxirane causes the epoxidation of the primary and secondary alkenylammonium arenesulfonates. The epoxidation is marked by high directing effect from ammonium group.