Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride

doi:10.1002/ejoc.200500834

CORC > 昆明植物研究所 > 中国科学院昆明植物研究所 > 植物化学与西部植物资源持续利用国家重点实验室

	Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride
	Ren, J ; Li, LC ; Liu, JK ; Zhu, HJ ; Pittman, CU
刊名	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
	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
内容类型	期刊论文
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.