Arene oxidation with malonoyl peroxides

Dragan, Andrei and Kubczyk, Tomasz M. and Rowley, Julian H. and Sproules, Stephen and Tomkinson, Nicholas C. O. (2015) Arene oxidation with malonoyl peroxides. Organic Letters, 17 (11). pp. 2618-2621. ISSN 1523-7060

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    Abstract

    Malonoyl peroxide 7, prepared in a single step from the commercially available diacid, is an effective reagent for the oxidation of aromatics. Reaction of an arene with peroxide 7 at room temperature leads to the corresponding protected phenol which can be unmasked by aminolysis. An ionic mechanism consistent with the experimental findings and supported by isotopic labeling, Hammett analysis, EPR investigations, and reactivity profile studies is proposed.