Methano- and Propanofullerenes by [1+2] and [3+2] Cycloadditions of Vinylcarbene Species

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Abstract

Vinylcarbene species generated by thermolysis of cyclopropenone acetal (CPA) reacts with C<sub>60</sub> in a [1 + 2] and a [3 + 2] manner to afford, at 80 °C, methano- and propanofullerene derivatives as a 10 : 1 mixture. The periselectivity depends on the reaction temperature; the ratio of the [1 + 2] and [3 + 2] cycloadducts changed to 2 : 1 and to 7 : 93 in the reaction at 100 and 140 °C, respectively. Temperature dependence was also observed in the reaction of phenyl-substituted CPA. The reactions of ethyl- and trimethylsilyl-substituted CPAs, which proceeded only at 150—170 °C, afforded propanofullerenes as a sole product. The reaction of the substituted CPAs proceeded exclusively via a terminally substituted vinylcarbene species.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 68(3), 935-941, 1995-03-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008887901
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    Journal Article
  • ISSN
    00092673
  • Data Source
    CJP  CJPref  J-STAGE 
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