Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride
Ren, J; Li, LC; Liu, JK; Zhu, HJ; Pittman, CU
Corresponding Authorhjzhu@mail.kib.ac.cn
2006-04-10
Source PublicationEUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN1434-193X
Issue8Pages:1991-1999
AbstractThe 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).
KeywordChemoselective Reductions Borohydride Amides B3lyp Transition States
Subject AreaChemistry, Organic
DOI10.1002/ejoc.200500834
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000236838800021
Citation statistics
Cited Times:4[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/2843
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.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
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.
Files in This Item: Download All
File Name/Size DocType Version Access License
201111010085.pdf(197KB) 开放获取--View Download
Related Services
Recommend this item
Bookmark
Usage statistics
Export to Endnote
Google Scholar
Similar articles in Google Scholar
[Ren, J]'s Articles
[Li, LC]'s Articles
[Liu, JK]'s Articles
Baidu academic
Similar articles in Baidu academic
[Ren, J]'s Articles
[Li, LC]'s Articles
[Liu, JK]'s Articles
Bing Scholar
Similar articles in Bing Scholar
[Ren, J]'s Articles
[Li, LC]'s Articles
[Liu, JK]'s Articles
Terms of Use
No data!
Social Bookmark/Share
File name: 201111010085.pdf
Format: Adobe PDF
This file does not support browsing at this time
All comments (0)
No comment.
 

Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.