Improved methods for the oxidation of primary and secondary alcohols

Abstract

The two-stage procedure for the oxidation of secondary alcohol chloroformates by treatment with dimethyl sulphoxide and then with triethylamine has been much improved by the addition of an acid scavenger, conveniently 1,2-epoxypropane, in the first stage of the sequence.

In agreement with mechanistic considerations, treatment of cholestanol, or of its nitrite, with nitrosyl cations in the presence of hexamethyldisiloxane as acid scavenger gave an excellent yield of cholestanone.