Cycloaddition of Bis[3,3-bis(diethylamino)thioacryloyl] Disulfide with Alkynic Dienophiles : A New Access to 2H-Thiopyran-2-thiones

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Abstract

The reaction of bis[3,3-bis(diethylamino)thioacryloyl] disulfide (<b>1</b>) with dimethyl acetylenedicarboxylate gave dimethyl 4-diethylamino-2-thioxo-2<i>H</i>-thiopyran-5,6-dicarboxylate in 69% yield. Similarly, a series of alkynic dienophiles reacted with <b>1</b> to give the corresponding 2<i>H</i>-thiopyran-2-thione derivatives in modest-to-reasonable yields. A full experimental description of this 2<i>H</i>-thiopyran-2-thione formation is given and a mechanism involving [4+2]cycloaddition followed by homolytic cleavage of the S–S bond is presented.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 69(7), 2091-2094, 1996-07-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008906481
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4060476
  • NDL Source Classification
    ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-B35
  • Data Source
    CJP  NDL  J-STAGE 
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