安定に単離できる5員環アルキン化合物 Stable Five-Membered Cyclic Alkynes

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It is generally known that small cyclic alkynes such as cyclopentyne is extremely reactive and unstable. Therefore it has been believed impossible to isolate cyclopentyne compounds.<BR>We recently reported that low-valent group 4 metallocenes reacted with 1, 2, 3-butatrienes to give 1-metallacyclopent-3-yne complexes and that resulted compounds are surprisingly stable and isolable. We succeeded in determination of their molecular structures by X-ray diffraction analyses, and showed that these are five-membered cyclic alkynes, while π, π-interaction of butatriene was also suggested. In this review, the preparation, structure and reactivity of these 1-metallacyclopent-3-yne compounds are described.<BR>The 1-zirconacyclopent-3-yne complexes reacted with another 'zirconocene' to form bimetallic complexes in which the cyclic alkyne coordinated to the other zirconocene moiety, indicating that the zirconacyclopentyne behaved as an alkyne. Seven-membered cyclic alkynes were also prepared from 1, 2, 3-butatriene and a zirconocene-alkyne compound. Protonolysis and subsequent nucleophilic attack to aldehyde gave allenyl or dienyl alcohol depending on proton source.

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  • 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 65(4), 347-357, 2007-04-01

    The Society of Synthetic Organic Chemistry, Japan

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各種コード

  • NII論文ID(NAID)
    10018898823
  • NII書誌ID(NCID)
    AN0024521X
  • 本文言語コード
    JPN
  • 資料種別
    ART
  • ISSN
    00379980
  • NDL 記事登録ID
    8788689
  • 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
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    CJP書誌  NDL  J-STAGE 
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