Reaction of Tri- and Tetrasubstituted Alkenes with the Low-Temperature Oxidizing System Aluminum tert-Butylate-tert-Butyl Hydroperoxide

The system consisting of aluminum tert-butylate and tert-butyl hydroperoxide under mild conditions (20°C) oxidizes tri- and tetrasubstituted ethylenes containing at least one -methyl group. The reaction proceeds via formation of tertiary allylic hydroperoxides and their subsequent transformations into unsaturated alcohols and epoxy alcohols, and also into carbonyl compounds. The presence of the latter products suggests degradation of the carbon skeleton of alkenes.