Reactions of Polychlorobenzenes with Alkanethiol Anions in HMPA. A Simple, High-Yield Synthesis of Poly(alkylthio)benzenes

Article abstract of DOI:10.1021/jo01310a022

Reactions of the isomeric trichlorobenzenes and tetrachlorobenzenes and of pentachloro- and hexachlorobenzene with an excess of the sodium salt of the isopropanethiol, in HMPA, afforded the products of complete displacement of all the chlorine atoms present in the molecule.Similar substitutions were also obtained with EtSNa.The reactions with MeSNa were in some cases complicated by the competitive nucleophilic attack at the methyl group of the initially formed aryl methyl thioethers which are thus demethylated to afford thiophenols.