Boomerang-type substitution reaction: Reactivity of fullerene epoxides   and a halofullerenol

doi:10.1002/asia.200600268

CORC > 北京大学 > 化学与分子工程学院

	Boomerang-type substitution reaction: Reactivity of fullerene epoxides and a halofullerenol
	Jia, Zhenshan ; Zhang, Xiang ; Zhang, Gaihong ; Huang, Shaohua ; Fang, Hao ; Hu, Xiangqing ; Li, Yuliang ; Gan, Liangbing ; Zhang, Shiwei ; Zhu, Daoben
刊名	chemistry an asian journal
	2007
关键词	epoxides fullerenes halohydrins peroxides single-electron transfer OPEN-CAGE FULLERENES NUCLEOPHILIC-SUBSTITUTION ELECTRON-TRANSFER MIXED PEROXIDES MOLECULAR-HYDROGEN ALIPHATIC-AMINES C-60 DERIVATIVES CATION FUNCTIONALIZATION
DOI	10.1002/asia.200600268
英文摘要	The C-symmetric fullerene chlorohydrin C-60(Cl)(OH)(OOtBu)(4) reacts with 4-dimethylaminopyridine (DMAP) and 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield two isomers with the formula C-60(O)-(OOtBu)(4) in good yields. These isomers differ with respect to the location of the epoxy functionality. The one from DMAP is C, symmetric, whereas that from DABCO is C, symmetric with the epoxy group on the central pentagon. Two different mechanisms are proposed to explain the chemoselectivity of these reactions. The reaction with DMAP involves single-electron transfer as the key step; DMAP acts as the electron donor. A combination of an oxygen-atom shift and S(N)2" processes (boomerang substitution) are responsible for the formation of isomer with DACBO. Various related reactions support the proposed mechanisms. The structures of new fullerene derivatives were determined by spectroscopy, single-crystal X-ray analysis, and chemical correlation experiments.; Chemistry, Multidisciplinary; SCI(E); 0; ARTICLE; 2; 290-300; 2
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/250788]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Jia, Zhenshan,Zhang, Xiang,Zhang, Gaihong,et al. Boomerang-type substitution reaction: Reactivity of fullerene epoxides and a halofullerenol[J]. chemistry an asian journal,2007.
APA	Jia, Zhenshan.,Zhang, Xiang.,Zhang, Gaihong.,Huang, Shaohua.,Fang, Hao.,...&Zhu, Daoben.(2007).Boomerang-type substitution reaction: Reactivity of fullerene epoxides and a halofullerenol.chemistry an asian journal.
MLA	Jia, Zhenshan,et al."Boomerang-type substitution reaction: Reactivity of fullerene epoxides and a halofullerenol".chemistry an asian journal (2007).