"Syn-Effect" in the Conversion of (E)-α, β-Unsaturated Esters to the Corresponding β, γ-Unsaturated Esters

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著者

    • GUHA Samar Kumar
    • Department of Chemical Science, Graduate School of Natural Science and Technology, Kanazawa University
    • SHIBAYAMA Atsushi
    • Department of Chemical Science, Graduate School of Natural Science and Technology, Kanazawa University
    • ABE Daisuke
    • Department of Chemical Science, Graduate School of Natural Science and Technology, Kanazawa University
    • UKAJI Yutaka
    • Department of Chemical Science, Graduate School of Natural Science and Technology, Kanazawa University
    • INOMATA Katsuhiko
    • Department of Chemical Science, Graduate School of Natural Science and Technology, Kanazawa University

抄録

The stereochemistry in the conversion of (<I>E</I>)-α,β-unsaturated esters to the corresponding β,γ-unsaturated esters by treatment with lithium hexamethyldisilazide in the presence of HMPA was investigated. The <I>Z</I>/<I>E</I> ratios of the resulting β,γ-unsaturated esters varied according to the γ-substituents of the (<I>E</I>)-α,β-unsaturated esters. This phenomenon was rationalized by "<I>syn-effect</I>" which may be attributed primarily to σ→π<SUP>*</SUP> interaction and/or 6π-electron homoaromaticity.

収録刊行物

  • Chemistry letters

    Chemistry letters 32(8), 778-779, 2003-08-05

    The Chemical Society of Japan

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各種コード

  • NII論文ID(NAID)
    10012818859
  • NII書誌ID(NCID)
    AA00603318
  • 本文言語コード
    ENG
  • 資料種別
    SHO
  • ISSN
    03667022
  • データ提供元
    CJP書誌  J-STAGE 
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