Electrochemical Reduction of Aromatic Sulfinic Acids in Dimethylsulfoxide

Abstract

The electrochemical reduction of benzenesulfinic, p-toluenesulfinic, and p-nitrobenzenesulfinic acids was studied in dimethylsulfoxide solutions. From cyclic voltammetry experiments, a chemical reaction following the first electron transfer was detected during the reduction process. A cyclic voltammetry technique using ultramicroelectrodes has provided kinetic parameters for the electron-transfer steps, from which it was possible to observe the influence of the ring substituent on the electrochemical reduction. The mechanism of the electroreduction of aromatic sulfinic acids in dimethylsulfoxide depends upon the nucleophilic attack of the radical anion produced on the starting compound during the reduction processes.

Electrochemical evidence of sulfinic acid derivative as an intermediate in the reduction of aromatic sulfonyl chloride in an aprotic medium

“…A few years ago, Angelo and Stradiotto [7] proposed a mechanism for the electrochemical reduction of aromatic sulfinic acids in an aprotic medium, demonstrating the importance of the chemical reactions of derivative intermediates.…”