Boomerang-type substitution reaction: Reactivity of fullerene epoxides and a halofullerenol
文献类型：期刊论文
| 作者 | 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
 |
| 出版日期 | 2007 |
| 卷号 | 2期号:2页码:290-300 |
| 关键词 | Epoxides Fullerenes Halohydrins Peroxides Single-electron Transfer |
| ISSN号 | 1861-4728 |
| 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. |
| 语种 | 英语 |
| WOS记录号 | WOS:000244337900009 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/60349]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Gan, Liangbing |
| 作者单位 | 1.Chinese Acad Sci, Inst Chem, Key Lab Organ Solids, Beijing Natl Lab Mol Sci, Beijing 100080, Peoples R China 2.Peking Univ, Minist Educ, Kay Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China |
| 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,2007,2(2):290-300. |
| 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,2(2),290-300. |
| MLA | Jia, Zhenshan,et al."Boomerang-type substitution reaction: Reactivity of fullerene epoxides and a halofullerenol".CHEMISTRY-AN ASIAN JOURNAL 2.2(2007):290-300. |
入库方式： OAI收割
来源：化学研究所
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