Oxidation Adjacent to Oxygen of Ethers

Abstract

In the presence of certain oxidants, ethers possessing at least one CH bond at the position adjacent to oxygen are susceptible to oxidation. The light-induced oxidation of diethyl ether in air is a well-known example of this phenomenon. In most instances, oxidative attack leads, via the intermediacy of carbonium ions or free radicals, to either esters (or lactones) or α-substituted ethers. Subsequent breakdown under the reaction conditions may then lead to mixtures of cleavage products, which can in turn suffer further oxidation. In principle, therefore, a wide range of products can result during the oxidation of an ether, depending on the nature of the substrate, the oxidant and the experimental conditions employed.