Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions - synthesis of halohydrins and epoxides

beta-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br+ and I+ ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave alpha-halocarbonyl compounds.