Oxidative Generation of 1-Nitroalkyl Radicals and Their Addition Reaction to Olefins^#

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Abstract

1-Nitroalkyl radicals are generated by oxidation of potassium salt of 1-<i>aci</i>-nitroalkanes with ammonium hexanitratocerate(IV). When the oxidation is carried out in the presence of electron-rich olefins, such as silyl enol ethers, intermolecular addition of the radicals onto the olefins proceeds to afford <i>β</i>-nitro ketones, which are further converted to <i>α</i>,<i>β</i>-unsaturated ketones in high yield. Stereoselective construction of fused ring systems is achieved by intramolecular addition of 1-nitroalkyl radicals.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 70(10), 2525-2534, 1997-10-15

    Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008924427
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4326362
  • NDL Source Classification
    ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-B35
  • Data Source
    CJP  NDL  IR  J-STAGE 
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