Hydroxy Group-Directed Homolytic Hydrostannylation of Alkenols with Dibutylchlorostannane

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著者

    • MIURA Katsukiyo
    • Department of Chemistry and Graduate School of Chemistry, University of Tsukuba
    • SAITO Hiroshi
    • Department of Chemistry and Graduate School of Chemistry, University of Tsukuba
    • UCHINOKURA Shingo
    • Department of Chemistry and Graduate School of Chemistry, University of Tsukuba
    • HOSOMI Akira
    • Department of Chemistry and Graduate School of Chemistry, University of Tsukuba

抄録

In homolytic hydrostannylation of allyl alcohol <B>1a</B> or homoallyl alcohol <B>1b</B>, dibutylchlorostannane (Bu<SUB>2</SUB>ClSnH) exhibited a much higher reactivity than tributylstannane (Bu<SUB>3</SUB>SnH). Competitive reaction of <B>1a</B> <I>vs</I>. 1-octene with Bu<SUB>2</SUB>ClSnH led to the selective formation of γ-stannylated alcohol <B>3a</B>. Hydrostannylation of 1,5-hexadien-3-ol (<B>8</B>) with Bu<SUB>2</SUB>ClSnH favored 1-stannylated product <B>9</B> over 6-stannylated product <B>10</B>, while the use of Bu<SUB>3</SUB>SnH decreased the regioselectivity.

収録刊行物

  • Chemistry letters

    Chemistry letters 1999(7), 659-660, 1999-07-05

    The Chemical Society of Japan

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各種コード

  • NII論文ID(NAID)
    10004702308
  • NII書誌ID(NCID)
    AA00603318
  • 本文言語コード
    ENG
  • 資料種別
    OTR
  • ISSN
    03667022
  • データ提供元
    CJP書誌  J-STAGE 
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