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题名: Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride
作者: Ren, J; Li, LC; Liu, JK; Zhu, HJ; Pittman, CU
刊名: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
关键词: chemoselective reductions ; borohydride ; amides ; B3LYP ; transition states
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).
出版日期: 2006-04-10
期号: 8, 页码:1991-1999
DOI标识: 10.1002/ejoc.200500834
语种: 英语
ISSN号: 1434-193X
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内容类型: 期刊论文
URI标识: http://ir.kib.ac.cn/handle/151853/2843
Appears in Collections:植物化学与西部植物资源持续利用国家重点实验室_期刊论文

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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

Recommended Citation:
Ren, J; Li, LC; Liu, JK; Zhu, HJ; Pittman, CU.Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride,EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2006,(8):1991-1999
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