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Synthesis 1994; 1994(9): 915-916
DOI: 10.1055/s-1994-25602
short paper
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Heterogeneous Permanganate Oxidations; Part 6: Selective Oxidation of Arenes

Dongyuan Zhao* , Donald G. Lee
  • *Department of Chemistry, University of Regina, Regina S4S OA2 Canada
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Publication Date:
17 September 2002 (online)

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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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