Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Stereospecific Synthesis of 2,4-Dienoci Acid Derivatives from Vinylmercuric Chlorides and Acrylic Acid Derivatives by Palladium(II) Salt

  • Kim Jin Il (Department of Industrial Chemistry, Hanyang University) ;
  • Lee Jong Tae (Department of Industrial Chemistry, Hanyang University)
  • Published : 1986.12.20
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Abstract

The reaction of (E)- or (Z)-1-alkenylmercuric chlorides with acrylic acid derivatives in the presence of 10 mol% of lithium trichloropalladate ($LiPdCl_3$) and an equimolar amount of cupric chloride, as a reoxidant for the palladium, in acetonitrile at room temperature gave the corresponding (E,E)- or (E,Z)-2,4-dienoic acid derivatives stereospecifically in moderate to good yields. The reaction of (E)- or (Z)-3-chloromercuripropenoic acid with olefins under the reaction condintion described above similarly gave good yields of (E,E)- or (Z,E)-2,4-dienoic acids stereospecifically. A side reaction, the homocoupling of alkenylmercuric chlorides, could be minimized by employing the condition described above. However, in the reaction of 3-chloromercuripropenoic acid with olefins under the present condition, the homocoupled side reaction product was not produced.

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