Potassium permanganate adsorbed on alumina selectively oxidizes arenes at the benzylic position. If the benzyl carbon is secondary, ketones are obtained in good yields; alcohols are produced if the benzylic position is tertiary. Benzopyranoid and benzofuranoid systems exhibit highly selective oxidation patterns. Decarboxylation occurs when phenylacetic acid is oxidized, but not when the corresponding ester, ethyl phenylacetate, is oxidized to ethyl benzoylformate.
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|Published - 1 Jan 1994