Cathodic Cleavage of Some Aryl Phenacyl Sulfides

Article abstract of DOI:10.1246/bcsj.58.1262

The electrolytic reduction of some aryl phenacyl sulfides in aqueous ethanol and anhydrous acetonitrile solutions has been investigated by means of polarography and controlled potential electrolysis.Dc polarograms of these compounds exhibit two waves in all solutions studied, the first of which corresponds to a one-electron and two-electron transfer depending upon the absence and presence of proton donor.The electrode reaction taking place at the first reduction step involves cleavage of the carbon-sulfur bond, resulting in formation of acetophenone and the corresponding thiols in good yields even in acetonitrile solution containing no proton donor.The second reduction step corresponds to the reduction of the acetophenone produced.