ELECTROCHEMICAL REDUCTION OF ACTIVATED OLEFINS IN DEUTERIATED SOLVENTS - II - A REGIOSELECTIVE DEUTERIATION CATALYTIC PROCESS FROM ALPHA,BETA-ETHYLENIC ARYL SULFONES

The title compounds were electrochemically reduced in aprotic dimethyl sulfoxide-d(6), acetonitrile-d(3), or organic solvents containing hea vy water. When a catalytic amount of charge passed through the cell, a lpha-deuteriation of olefins occurred in high yield. Since both chemic al and electrochemically formed bases were found to be totally ineffic ient in the performance of such deuteriation, a radical chain process is tentatively proposed. During attempted total reduction of substrate s, tetradeuteriated dimers were isolated, from which information on th e reduction mode and coupling process can be obtained.