The electrochemical oxidation of dimethyl disulfide - Anodic methylsulfanylation of phenols and aromatic ethers

The electrochemical oxidation of dimethyl disulfide was investigated in acetonitrile and dichloromethane. The nature of the oxidation strongly depends on the nucleophilicity of the solvent. In acetonitrile a one-electron oxidation is observed and the consecutive species did not exhibit any reactivity towards aromatic compounds subject to electrophile substitution. On the contrary, the oxidation of dimethyl disulfide in methylene chloride afforded a two-electron process with the formation of a species consistent with CH3-S+. Its reactivity towards phenols and aromatic ethers was confirmed and showed a selective monomethylsulfanylation in most of the cases. (C) 2005 Elsevier Ltd. All rights reserved.