A Photochemical Sequence for Oxidation of Alcohols to Carbonyl Compounds

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Abstract
In the early nineteen sixties the photochemical reactions of three esters of pyruvic acid were reported1,2 (equation 1). The products from these reactions suggested that pyruvate formation followed by photochemical reaction could be a new technique for oxidation of alcohols to carbonyl compounds. At the time, the forcing conditions necessary for esterification of pyruvic acid3 would have discouraged further consideration of pyruvate photolysis as a part of a mild oxidation process. The recent report of a facile synthesis of the acid chloride of pyruvic acid4 raised the possibility that the esterification-photoreaction sequence for oxidation could become a useful synthetic tool. This new reaction sequence now has been investigated for a series of alcohols and found to be a promising oxidation pathway.