The structures of enol benzoates of substituted dibenzoylmethanes have been determined: in all cases benzoylation occurs at the carbonyl oxygen atom adjacent to the more electron-withdrawing aryl group. Benzoylacetone forms isomeric E- and Z-enol acetates and benzoates, reaction occurring at the oxygen atom of the acetyl group. A mechanism for the formation of enol benzoates of β-diketones is proposed.
J. Larkin, M. G. Murray, D. C. Nonhebel and A. D. Mitchell, J. Chem. Soc., Perkin Trans. 1, 1976, 380 DOI: 10.1039/P19760000380
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