ビニル炭素におけるS_N2反応 Vinylic S_N2 Reaction

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著者

    • 奥山 格 OKUYAMA Tadashi
    • 兵庫県立大学大学院物質理学研究科 Department of Material Science, Graduate School of Material Science, Himeji Institute of Technology, University of Hyogo

抄録

Vinylic nucleophilic substitution via a concerted bimolecular mechanism (S<SUB>N</SUB>V 2), which has long been rejected as a possible pathway, has recently been found to be feasible both theoretically and experimentally. Two S<SUB>N</SUB>V 2 mechanisms are possible : one is designated as S<SUB>N</SUB>Vσ where nucleophilic attack takes place in a molecular plane at the σ<SUP>*</SUP> orbital resulting in inversion of configuration, while the other as S<SUB>N</SUB>Vπ which involves out-of-plane π<SUP>*</SUP> attack of a nucleophile leading to stereochemical retention. Both modes of the concerted S<SUB>N</SUB>V 2 reactions were found for vinyl iodonium salts, and detailed mechanistic investigations are summarized. Intramolecular S<SUB>N</SUB>Vσ reactions were more often observed, and applied to some synthesis of cyclic compounds. Those observations are rationalized by high level ab initio MO calculations.

収録刊行物

  • 有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN  

    有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN 64(4), 348-358, 2006-04-01 

    The Society of Synthetic Organic Chemistry, Japan

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各種コード

  • NII論文ID(NAID)
    10018131487
  • NII書誌ID(NCID)
    AN0024521X
  • 本文言語コード
    JPN
  • 資料種別
    REV
  • ISSN
    00379980
  • NDL 記事登録ID
    7921716
  • NDL 雑誌分類
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL 請求記号
    Z17-256
  • データ提供元
    CJP書誌  NDL  J-STAGE 
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