Synthesis and Functionalization of Symmetrical 2,5-Diaryl Fulleropyrrolidines: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Arylmethanamines

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• 作者：Ji-Long Shi ; Fa-Bao Li ; Xiao-Feng Zhang ; Jun Wu ; Hong-Yu Zhang ; Jie Peng ; Chun-Xiang Liu ; Li Liu ; Ping Wu ; Jia-Xing Li
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：March 4, 2016
• 年：2016
• 卷：81
• 期：5
• 页码：1769-1777
• 全文大小：451K
• ISSN：1520-6904

文摘

A series of scarce N-unsubstituted 2,5-diaryl fulleropyrrolidines as cis isomers could be prepared via the facile one-step reaction of [60]fullerene with N-unsubstituted arylmethanamines promoted by cheap and easily available ferric perchlorate. Nevertheless, the reaction of N-substituted arylmethanamines with [60]fullerene under the same conditions gave different experimental results. N-Methylbenzylamine formed N-methyl 2,5-diphenyl fulleropyrrolidine as a trans isomer, and N,N-dibenzylamine unexpectedly afforded the N-unsubstituted 2,5-diphenyl fulleropyrrolidine as a cis isomer. Intriguingly, high stereoselectivity for all 2,5-diaryl fulleropyrrolidines could be observed although both cis and trans isomers were possibly formed. N-Unsubstituted fulleropyrrolidine could be further converted to N-substituted fulleropyrrolidines under the assistance of an acid chloride or an isocyanate. A possible reaction pathway leading to 2,5-diaryl fulleropyrrolidines is also proposed.