Electrochemical Reduction of 4-Iodophenyl Sulfonyl Chloride

Abstract

Important aspects of the electrochemical reduction of 4-iodophenyl sulfonyl chloride are investigated in acetonitrile at a glassy carbon electrode. The first electron transfer follows a concerted process where the S-Cl chemical bond is cleaved upon injection of the first electron. An interesting autocatalytic mechanism is encountered and the 4-iodophenyl sulfonyl chloride is reduced both at the electrode and through homogeneous electron transfer from the resulting sulfinate anion. An electron transfer between the generated sulfinate anion and the parent molecule is the basis to the observed autocatalytic process. Consequently, the reduction process depends on both the concentration of the substrate and the scan rate. Gas phase chemical quantum calculations results help to rationalize the mechanism of the first electron transfer.