Hypervalent Iodine Reagent Mediated Reaction of [60]Fullerene with Amines

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• 作者：Chun-Bao Miao ; Xin-Wei Lu ; Ping Wu ; Jiaxing Li ; Wen-Long Ren ; Meng-Lei Xing ; Xiao-Qiang Sun ; Hai-Tao Yang
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：December 6, 2013
• 年：2013
• 卷：78
• 期：23
• 页码：12257-12262
• 全文大小：322K
• 年卷期：v.78,no.23(December 6, 2013)
• ISSN：1520-6904

文摘

The hypervalent iodine reagent mediated reaction of C₆₀ with various readily available amines for the easy preparation of iminofullerenes has been developed. The reaction between C₆₀ and sulfonamides can be effectively controlled to selectively synthesize azafulleroids or aziridinofullerenes under PhI(OAc)₂/I₂ or PhIO/I₂/CuCl/lutidine conditions, respectively. For phosphamide and urea, only one isomer is obtained. However, carbamate gives three kinds of products. Interestingly, the reaction of C₆₀ with alkylamines allows the effective synthesis of aziridinofullerenes and regioselective cis-1-bisaziridinofullerenes.