Regio- and Stereo-Chemistry of Addition of Molecular Bromine to S-Oxidized Derivatives of 3, 4-Di-t-butylthiophene : Exclusive 1, 4-Cis-Additions

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Bromine added to the 1-oxide, 1,1-dioxide, and sulfoximide derivatives of 3,4-di-<i>t</i>-butylthiophene exclusively in a 1,4-<i>cis</i>-addition mode. Thus, bromine added to 3,4-di-<i>t</i>-butylthiophene 1-oxide at room temperature in CH<sub>2</sub>Cl<sub>2</sub> to give the 1,4-<i>cis</i>-adducts exclusively. The adducts are composed of two compounds in the ratio 57 : 43, where the major one is the <i>anti</i>-adduct respective to the S=O bond and the minor one is the <i>syn</i>-adduct. Addition of bromine to 3,4-di-<i>t</i>-butylthiophene 1,1-dioxide gave the 1,4-<i>cis</i>-adduct as the sole product. Addition of bromine to the <i>N</i>-tosyl substituted sulfoximide derivative of 3,4-di-<i>t</i>-butylthiophene afforded the single 1,4-<i>cis</i>-adduct in which two bromine atoms are <i>anti</i> to the <i>N</i>-tosyl group. Bromine added to the <i>N</i>-unsubstituted sulfoximide derivative of 3,4-di-<i>t</i>-butylthiophene to produce the 1,4-<i>cis</i>-addition products exclusively, which are a 67 : 33 mixture of the <i>anti</i>- and <i>syn</i>-adducts to the S=O bond.

収録刊行物

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 76(3), 619-625, 2003-03-15

    公益社団法人 日本化学会

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各種コード

  • NII論文ID(NAID)
    10012811320
  • NII書誌ID(NCID)
    AA00580132
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    00092673
  • データ提供元
    CJP書誌  J-STAGE 
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