Tetrachlorocyclopentadienone 0-Oxide, a Facile Oxygen-Atom-Transfer Reagent : The Disproportionation of Cycloalkyldioxyl Radicals

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Abstract

Photolysis of tetrachlorodiazocyclopentadiene (<b>1</b>) in oxygen-saturated hydrocarbon solvents results in the transient formation of tetrachlorocyclopentadienone <i>O</i>-oxide (<b>3</b>). This rapidly decomposes, giving rise to products derived from oxidation of the hydrocarbons. Cyclopentane, cyclopentene, cycloheptane, cycloheptene, cycloheptatriene, and indene have been studied. Cycloheptatriene and indene gave only low yields of tractable products, but the others gave the corresponding ketones and secondary alcohols as the major products. Although yields varied considerably, the ketone and alcohol products were always obtained, within experimental error, in a 1 : 1 molar ratio. This observed product ratio supports the disproportionation of cycloalkyldioxyl radicals as a crucial step.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 71(6), 1397-1400, 1998-06-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008933046
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4503967
  • 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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