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Synlett 1990; 1990(2): 87-88
DOI: 10.1055/s-1990-20994
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Reductive and Oxidative Alkylations of 1,4-Enediones by Alkylmercury Chlorides1

Glen A. Russell* , Byeong Hyo Kim
  • *Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA
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Publication Date:
08 March 2002 (online)

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The free radical chain reaction of alkylmercury halides with 1,4-enediones, for example diethyl maleate, diethyl fumarate, (E)-1,2-dibenzoylethylene and ethyl (E)-3-benzoylacrylate yields the saturated alkylation product when promoted by iodide or thiosulfate/iodide. In the presence of 1,4-diazabicyclo[2.2.2]-octane (DABCO) the intermediate enolyl radical can be deprotonated to a radical anion which yields the unsaturated alkylation product upon electron transfer to alkylmercury chloride.