Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride
文献类型：期刊论文
| 作者 | Ren, J; Li, LC; Liu, JK; Zhu, HJ; Pittman, CU |
| 刊名 | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2006-04-10 |
| 期号 | 8页码:1991-1999 |
| 关键词 | Chemoselective Reductions Borohydride Amides B3lyp Transition States |
| ISSN号 | 1434-193X |
| DOI | 10.1002/ejoc.200500834 |
| 通讯作者 | hjzhu@mail.kib.ac.cn |
| 文献子类 | Article |
| 英文摘要 | The mechanisms for the different chemoselectivities in sodium borohydride reactions with primary, secondary and tertiary amides have been investigated both at the B3LYP/631++G(d,p)//B3LYP/6-31G(d,p) and B3LYP/6-31++G(d,p)// HF/6-31G(d,p) levels of theory. The predicted structures of the key intermediates were then confirmed by experiments. Primary amides generate the corresponding nitriles when treated with sodium borohydride. Nitrile formation occurs by initial proton abstraction from the primary amide's nitrogen atom by a hydride ion, followed by loss of hydrogen and the coordination of the amide nitrogen atom to BH3. Three subsequent steps produce acetonitrile. The computational predictions agree well with the experimental results. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006). |
| 学科主题 | Chemistry, Organic |
| WOS关键词 | EXCHANGE-CORRELATION FUNCTIONALS ; SELECTIVE REDUCTION ; ORGANIC-COMPOUNDS ; METHYL-FLUORIDE ; S(N)2 REACTIONS ; REDUCING AGENT ; REACTIVITY ; HALIDES ; SYSTEM ; CONVENIENT |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000236838800021 |
| 公开日期 | 2011-12-19 |
| 源URL | [http://ir.kib.ac.cn:8080/handle/151853/2843]  |
| 专题 | 昆明植物研究所_植物化学与西部植物资源持续利用国家重点实验室 |
| 作者单位 | 1.CAS, Kunming Inst Bot, Organ Synth & Nat Prod Lab, Kunming 650204, Yunnan, Peoples R China 2.Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA |
| 推荐引用方式 GB/T 7714 | Ren, J,Li, LC,Liu, JK,et al. Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2006(8):1991-1999. |
| APA | Ren, J,Li, LC,Liu, JK,Zhu, HJ,&Pittman, CU.(2006).Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(8),1991-1999. |
| MLA | Ren, J,et al."Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .8(2006):1991-1999. |
入库方式： OAI收割
来源：昆明植物研究所
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