Cathodic Reduction of Negatively Substituted Ketones: α-Ketoacids and β-Ketoesters

Abstract

The cathodic reduction of -ketoacids and /3-ketoesters has been studied. The -carboxyl group in -ketoacids has been found to promote reduction but not pinacol formation compared with a phenyl group. It also has a pronounced effect upon the stereoisomeric identity of the pinacol product, unlike unsubstituted ketones. The carbethoxy group in /3-ketoesters inhibits pinacol formation in acid medium and favors hydroxy acid in alkaline medium.

Electrosynthesis of 2,3-dimethyltartaric acid from pyruvic acid in acid medium

“…In 1958 the electrosynthesis of 2,3-dimethyltartaric acid was studied on Cu(Hg) in ammonia. The maximum selectivity obtained was close to 11% [30].…”

Synthesis and properties of the .alpha.-keto acids

“…164 The cathodic reduction of pyruvic (3) and phenylglyoxylic (17) acids using Hg or Hg-Cu electrodes has been described. 299 The products vary according to the conditions, but generally in the case of pyruvic acid (3), a major product is lactic acid (165) with smaller amounts of dimethyl tartaric acid (166). In the case of phenylglyoxylic acid (17), a major product is meso-diphenyltartaric acid (167).…”