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

doi:10.1021/acs.joc.5b02412

CORC > 合肥物质科学研究院 > 中国科学院合肥物质科学研究院 > 中科院等离子体物理研究所

	Synthesis and Functionalization of Symmetrical 2,5-Diaryl Fulleropyrrolidines: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Arylmethanamines
	Shi, Ji-Long 1,2; Li, Fa-Bao 1,2; Zhang, Xiao-Feng 1,2; Wu, Jun 1,2; Zhang, Hong-Yu 1,2; Peng, Jie 1,2; Liu, Chun-Xiang 1,2; Liu, Li 1,2; Wu, Ping 3; Li, Jia-Xing 4
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2016-03-04
卷号	81 期号:5 页码:1769-1777
DOI	10.1021/acs.joc.5b02412
文献子类	Article
英文摘要	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.
WOS关键词	SOLVENT-FREE CONDITIONS ; AMINO-ACID ESTERS ; AZOMETHINE YLIDES ; RADICAL REACTIONS ; 1,3-DIPOLAR CYCLOADDITION ; BUCKMINSTERFULLERENE C-60 ; PHOTOCHEMICAL ADDITION ; FULLERENE CHEMISTRY ; PROMOTED REACTION ; TERTIARY-AMINES
WOS研究方向	Chemistry
语种	英语
WOS记录号	WOS:000371753900005
资助机构	National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; National Natural Science Foundation of China(21102041 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Foundation of Hubei Province(2014CFB550 ; Natural Science Fund for Creative Research Groups of Hubei Province of China(2014CFA015) ; Natural Science Fund for Creative Research Groups of Hubei Province of China(2014CFA015) ; Natural Science Fund for Creative Research Groups of Hubei Province of China(2014CFA015) ; 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内容类型	期刊论文
源URL	[http://ir.hfcas.ac.cn/handle/334002/21409]
专题	合肥物质科学研究院_中科院等离子体物理研究所
作者单位	1.Hubei Univ, Hubei Collaborat Innovat Ctr Adv Organ Chem Mat, Key Lab Synth & Applicat Organ Funct Mol, Minist Educ, Wuhan 430062, Peoples R China 2.Hubei Univ, Sch Chem & Chem Engn, Wuhan 430062, Peoples R China 3.Dezhou Univ, Key Lab Coordinat Chem & Funct Mat Univ Shandong, Coll Chem & Chem Engn, Dezhou 253023, Peoples R China 4.Chinese Acad Sci, Inst Plasma Phys, Key Lab Novel Thin Film Solar Cells, POB 1126, Hefei 230031, Peoples R China
推荐引用方式 GB/T 7714	Shi, Ji-Long,Li, Fa-Bao,Zhang, Xiao-Feng,et al. Synthesis and Functionalization of Symmetrical 2,5-Diaryl Fulleropyrrolidines: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Arylmethanamines[J]. JOURNAL OF ORGANIC CHEMISTRY,2016,81(5):1769-1777.
APA	Shi, Ji-Long.,Li, Fa-Bao.,Zhang, Xiao-Feng.,Wu, Jun.,Zhang, Hong-Yu.,...&Li, Jia-Xing.(2016).Synthesis and Functionalization of Symmetrical 2,5-Diaryl Fulleropyrrolidines: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Arylmethanamines.JOURNAL OF ORGANIC CHEMISTRY,81(5),1769-1777.
MLA	Shi, Ji-Long,et al."Synthesis and Functionalization of Symmetrical 2,5-Diaryl Fulleropyrrolidines: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Arylmethanamines".JOURNAL OF ORGANIC CHEMISTRY 81.5(2016):1769-1777.