Palladium-Catalyzed Elimination Reaction of Acyclic (<i>E</i>)-Allylic Acetates: The Stereochemistry Elucidated by “<i>Syn</i>-Effect”

  • Hiroyuki Takenaka
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Yutaka Ukaji
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Katsuhiko Inomata
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University

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<jats:title>Abstract</jats:title> <jats:p>The stereochemistry of the elimination reaction of acyclic (E)-allylic acetates into the corresponding 1,3-dienes catalyzed by palladium in the presence of a base was investigated. The Z/E ratios of the resulting 1,3-dienes varied with the δ-substituents of the starting allylic acetates. This phenomenon was discussed based on the concept of a “syn-effect,” which is most primarily rationalized by a σ → π* interaction.</jats:p>

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  • Chemistry Letters

    Chemistry Letters 34 (2), 256-257, 2005-01-22

    Oxford University Press (OUP)

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