Highly efficient oxygen transfer from tert-butyl hydroperoxide to benzylic carbons catalyzed by chromium(VI) oxide under high substrate/ hydroperoxide ratios

Abstract

Chromium(VI) oxide induces a quasi-quantitative transfer of one oxygen atom from t-BuOOH to a benzylic methylene group when a high ratio of substrate/hydroperoxide is employed, the corresponding carbonyl compound being the major oxidation compound. Hydroxylation and tert-butyl-peroxidation are the main reactions observed for a tertiary benzylic carbon. The interference of free benzylic radicals under these conditions is a minor reactive pathway.