Convenient preparation of aryl methyl and aryl phenyl sulfides from arenediazonium tetrafluoroborates and trimethyl(methylthio)- and trimethyl(phenylthio)silanes

Abstract

Aryl methyl and aryl phenyl sulfides were prepared by the reaction of arenediazonium tetrafluoroborates with trimethyl(methylthio)- and trimethyl(phenylthio)silanes, respectively. In the latter case, addition of cupric sulfide was found to increase the yields. The main by-products were protodediazoniated products and diphenyl disulfide, which can be removed by treatment with aqueous sulfide and a base.