Epoxidation of ethylenic linkages by chromic acid. I. Oxidation of 1,1,2-triphenylpropene-1 by chromic oxide

The oxidation of 1,1,2-triphenylpropene-1 by chromic oxide in acetic anhydride gives 1,2-epoxy-1,1,2-triphenylpropane with fission products and 2,3,3-triphenylprop-2-en-1-al. The epoxide is relatively stable towards aqueous sulphuric acid. Chromic acid in aqueous sulphuric acid brings about oxidative fission of the double bond together with the formation of the above unsaturated aldehyde. A mechanism for the epoxidation of olefins in chromic acid is discussed.