The mechanism of oxidation of α-glycols by periodic acid. Part VII. General acid–base catalysis in the oxidation of pinacol, and reaction in alkaline solution

Abstract

The oxidation of pinacol by periodic acid is catalysed by general acids and bases, the catalysed step being cyclisation of a periodate monoester. With ammonia this step is so accelerated that the formation of the monoester becomes partially rate-limiting. The mechanism of the oxidation in both buffered and unbuffered solutions is discussed, and the occurrence of the rate maximum at pH 9 is explained.