The Oxidation of Acetals by Ozone

Abstract

Ozone reacts very smoothly with acetals to give the corresponding esters. There are six gauche conformations that are theoretically possible for an acetal function. It is shown that only three of them are reactive toward ozone. It is proposed that a reactive acetal function must take a conformation in which each oxygen must have an electron pair orbital oriented antiperiplanar to the C—H bond. The mechanism of this reaction is also discussed.