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

• Hidetoshi Tokuyama

  Department of Chemistry, Tokyo Institute of TechnologyMeguro, Tokyo 152

• Hiroyuki Isobe

  Department of Chemistry, Tokyo Institute of TechnologyMeguro, Tokyo 152

• Eiichi Nakamura

  Department of Chemistry, Tokyo Institute of TechnologyMeguro, Tokyo 152

抄録

Vinylcarbene species generated by thermolysis of cyclopropenone acetal (CPA) reacts with C60 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.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 68 (3), 935-941, 1995-03-01

  Oxford University Press (OUP)

キーワード

• General Chemistry

詳細情報

• CRID: 1360565169057659776
• NII論文ID: 10008887901
• NII書誌ID: AA00580132
• DOI: 10.1246/bcsj.68.935
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/68/3/935/56191525/bcsj.68.935.pdf
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