Reaction of C-60(2-) with Organic Halides Revisited in DMF: Proton Transfer from Water to RC60- and Unexpected Formation of 1,2-Dihydro[60]fullerenes
文献类型：期刊论文
| 作者 | Yang WW ; Li ZJ ; Gao XA |
| 刊名 | journal of organic chemistry
 |
| 出版日期 | 2010 |
| 卷号 | 75期号:12页码:4086-4094 |
| 关键词 | ELECTRON-TRANSFER ELECTROCATALYTIC REDUCTION SUPRAMOLECULAR COMPLEX FULLERENE CHEMISTRY SELECTIVE SYNTHESIS GAMMA-CYCLODEXTRIN GRIGNARD-REAGENTS APROTIC-SOLVENTS ANIONIC C-60 ELECTROSYNTHESIS |
| ISSN号 | 0022-3263 |
| 通讯作者 | gao xa |
| 中文摘要 | the reactions of dianionic c-60 with organic halides, which have been studied extensively in benzonitrile (phcn), are revisited in a different solvent medium, n,n-dimethylformamide (dmf), by using arch2br (ar = ph, c6h4ch3, c6h4br). interestingly, instead of the 1,4-r2c60 adducts, which are the typical products when the reactions are carried out in phcn, the 1,2-dihydro[60]fullerenes (1,2-hrc60) have been obtained as the major products in dmf, except for the case of o-ch3c6h4ch2br probably due to the steric effect. the obtained 1,2-dihydro[60]fullerenes have been characterized with single-crystal diffraction, h-1 and c-13 nmr, high-resolution mass spectrometry (hrms), and uv-vis. further examination with deuterated reagents including plicd(2)br, dmf-d(7), and d2o has revealed that the fullerenyl hydrogen of 1,2-dihydrofullerenes originates from traces of water residue in dmf. when the reaction is re-examined in phcn with the addition of an excessive amount of water, the yield of 1,2-dihydrofullerene increases significantly, but is still lower compared with that obtained in dm f, demonstrating a considerable solvent effect on the reactivity of c-60(2-). a possible mechanism accounting for such a difference is proposed. the work has presented an alternative protocol for effective preparation of 1,2-dihydro[60]fullerenes, and may also provide clues toward a better understanding of the proton transfer process for anionic coo-mediated reducing, reactions involving h2o. |
| 收录类别 | SCI收录期刊论文 |
| 语种 | 英语 |
| WOS记录号 | WOS:000278560700016 |
| 公开日期 | 2012-04-26 |
| 源URL | [http://ir.ciac.jl.cn/handle/322003/43667]  |
| 专题 | 长春应用化学研究所_长春应用化学研究所知识产出_期刊论文 |
| 推荐引用方式 GB/T 7714 | Yang WW,Li ZJ,Gao XA. Reaction of C-60(2-) with Organic Halides Revisited in DMF: Proton Transfer from Water to RC60- and Unexpected Formation of 1,2-Dihydro[60]fullerenes[J]. journal of organic chemistry,2010,75(12):4086-4094. |
| APA | Yang WW,Li ZJ,&Gao XA.(2010).Reaction of C-60(2-) with Organic Halides Revisited in DMF: Proton Transfer from Water to RC60- and Unexpected Formation of 1,2-Dihydro[60]fullerenes.journal of organic chemistry,75(12),4086-4094. |
| MLA | Yang WW,et al."Reaction of C-60(2-) with Organic Halides Revisited in DMF: Proton Transfer from Water to RC60- and Unexpected Formation of 1,2-Dihydro[60]fullerenes".journal of organic chemistry 75.12(2010):4086-4094. |
入库方式： OAI收割
来源：长春应用化学研究所
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