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

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journal contribution
posted on 06.12.2013, 00:00 by Chun-Bao Miao, Xin-Wei Lu, Ping Wu, Jiaxing Li, Wen-Long Ren, Meng-Lei Xing, Xiao-Qiang Sun, Hai-Tao Yang
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.