中华医学超声杂志

应用化学 ›› 2010, Vol. 27 ›› Issue (01): 1-11.

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有机富勒烯化合物的逆环加成反应

李芳芳1,2,高翔1*   

  1. (1.中国科学院长春应用化学研究所电分析化学国家重点实验室 长春 130022;
    2.中国科学院研究生院 北京)
  • 收稿日期:2009-01-03 修回日期:2008-12-26 出版日期:2010-01-10 发布日期:2010-01-10
  • 通讯作者: 高翔，男，研究员，博士生导师; E-mail:xgao@ciac.jl.cn; 研究方向：富勒烯化学
  • 基金资助:
    国家自然科学基金(20972150)国家自然科学基金国际合作(00550110367，00650110171)资助项目

Retro-Cycloaddition Reaction of Organofullerenes

LI Fang-Fang1,2,GAO Xiang1*   

  1. (1.State Key Laboratory of Electroanalytical Chemistry,Changchun Institute of
    Applied Chemistry,Chinese Academy of Sciences,Changchun 130022;
    2.Graduate School of Chinese Academy of Sciences,Beijing)
  • Received:2009-01-03 Revised:2008-12-26 Published:2010-01-10 Online:2010-01-10

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摘要：

逆环加成反应是富勒烯衍生物的一种重要反应。在还原、氧化或加热条件下，许多富勒烯衍生物的加成基团会从富勒烯骨架上断开，得到富勒烯母体，是富勒烯环加成反应的逆反应。该反应与富勒烯环加成反应结合，已被应用于富勒烯化学中保护/去保护基团方法，对于选择性制备富勒烯及其衍生物具有重要意义。然而由于逆环加成反应的存在，引起了有机富勒烯化合物的不稳定，从而可能影响其在实际中的应用。最近，我们研究了一系列含有亚胺酯杂原子环结构的富勒烯噁唑衍生物在电化学还原下的稳定性，结果表明加成基团之间存在的分子内C-H…X（X = N，O）氢键对化合物的稳定性可能起着较为关键的作用。在此，我们将结合我们的工作对有机富勒烯化合物的逆环加成反应进行综述。

关键词: 富勒烯衍生物，逆环加成反应，C--H...X氢键

Abstract:

Retro-cycloaddition reaction is one of the most important reactions of fullerene derivatives. Many kinds of organofullerenes are not stable under reductive, oxidative or thermal conditions, where the functional addends are removed from the fullerene sphere and lead to the formation of pristine fullerenes. Such addition-retro-addition reaction has shown promising application in the protection/deprotection strategy for the purification and functionalization of fullerenes. However, the retro-addition reactions may cause problems for the applications of organofullerenes due to the instability of the compounds. Recently the electrochemical stabilities of a series of fullerooxazoles have been studied. The results show that there is intramolecular C-H…X (X = N，O) hydrogen bonding among the addends for one of the compounds, which attributes to the stability of the compound. Herein, the progress of the retro-cycloaddition reaction of organofullerenes and the factors that may affect the stability of organofullerenes is reviewed.

Key words: fullerene derivatives,retro-cycloaddition reactions,C--H...X hydrogen bonding

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