THE AUTOOXIDATION OF ORGANOMERCURIC SALTS

Abstract

It has been found that besides the homopolar bimolecular oxidation of alkylmercuric salts which has been reported previously an alternative unimolecular reaction of heteropolar character may occur. The product of this heteropolar reaction is the alkene, but it probably proceeds through an alkylmercury cation since reaction in benzene leads to the Friedel–Crafts type of product. Like the homopolar reaction, the heteropolar reaction is accelerated by electron withdrawal of the anionic part of the salt. Indeed, it is believed that both mechanisms are operative among many of the mercuric salt oxidations of alkenes which previously have been reported.