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Synthesis 1991; 1991(12): 1177-1179
DOI: 10.1055/s-1991-28415
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One-Flask Preparation of Symmetrical Ketones and 1,2-Diketones from Esters

George A. Olah* , An-hsiang Wu
  • *Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, USA
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Publikationsdatum:
29. April 2002 (online)

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A convenient one-flask preparation of a series of symmetrical 1,2diketones from esters is reported using sodium metal induced acyloin condensation followed by reaction with thionyl chloride. Symmetrical monoketones were obtained when after initial acyloin condensation, the reaction mixture is oxidized with aqueous sodium bromate and then reacted with thionyl chloride. Preparative aspects, the scope of the reaction, and the suggested mechanism are discussed.