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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 101, 1995 - Issue 1-4
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Original Articles

CONVENIENT PREPARATION OF UNSYMMETRICALLY SUBSTITUTED BENZILS BY PERMANGANATE OXIDATION OF β-OXO PHOSPHORUS YLIDES

R. Alan Aitken School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, UK; Department of Chemistry, University of Edinburgh, West Mains Road, Edinburgh, EH9 3JJ, United Kingdom
,
J. I. G. Cadogan Department of Chemistry, Imperial College of Science, Technology and Medicine, South Kensington, London, SW7 2AY, United Kingdom
&
Ian Gosney Department of Chemistry, University of Edinburgh, West Mains Road, Edinburgh, EH9 3JJ, United Kingdom
Pages 281-286 | Received 06 Dec 1994, Published online: 04 Oct 2006
 
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Abstract

Oxidative cleavage of a range of ylides 4 with R1 and/or R2 being aromatic groups, using KMnO4 in a two-phase system, affords unsymmetrical benzils and 1-arylpropane-1,2-diones 5 in moderate to good yield, and the ylide formation and oxidation can be combined in a convenient one-pot method.

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