Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride
Ren, J; Li, LC; Liu, JK; Zhu, HJ; Pittman, CU
2006-04-10
发表期刊EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN1434-193X
期号8页码:1991-1999
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).
关键词Chemoselective Reductions Borohydride Amides B3lyp Transition States
学科领域Chemistry, Organic
DOI10.1002/ejoc.200500834
收录类别SCI
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Organic
WOS记录号WOS:000236838800021
引用统计
被引频次:4[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/2843
专题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
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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.
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