Hydride ion transfer in oxidations of alcohols and ethers

Abstract

The rates of oxidation of various alcohols and ethers by bromine, permanganate, and mercury(II) have been measured. The observed easy oxidative fission of di-isopropyl ether, and the large accelerating effects of alkyl substituents, support mechanisms involving hydride ion transfer from the carbon atom bearing the functional group to the oxidant. Selective oxidation of an isopropyl ether function in the presence of a primary alcohol has been demonstrated.