Electrochemical reduction of some α-oxo-esters in methanol at a platinum cathode

Abstract

The reactivities towards cathodic reduction for some aliphatic and aromatic α-oxo-esters, in methanol, at a platinum cathode are reported. The relative rates for the reduction follow the order: α-oxovalerate > α-oxobutyrate > phenylglyoxylate > 4-chlorophenylglyoxylate > 4-methoxycarbonylphenylglyoxylate. No reduction occurred with oxomalonate, 4-methoxyphenylglyoxylate, or 4-nitrophenylglyoxylate. An explanation for these differences in reactivities is suggested on the basis of electronic effects, steric inhibition of coplanarity, and hemiacetal formation.