Document Detail


Studies on Elimination Pathways of β-Halovinyl Ketones Leading to Allenyl and Propargyl Ketones and Furans under the Action of Mild Bases.
MedLine Citation:
PMID:  23198987     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The elimination pathway of stereochemically defined β-halovinyl ketones has been investigated using a mild base NEt3, leading to the formation of allenyl ketones and propargyl ketones. A preferential α-vinyl enolization of (E)-β-chlorovinyl ketones has been observed where a non-planar s-cis conformation is proposed as a dominant conformation as opposed to a planar s-cis conformation of (Z)-β-chlorovinyl ketones. Other eliminative pathways such as concerted syn- and anti-E2 as well as γ-deprotonation are excluded based on the deuterium isotope studies. The synthetic utility of the elimination reaction of β-chlorovinyl ketones was further demonstrated for a one-pot synthesis of 2,5-disubstituted furans in the presence of 1mol% of CuCl.
Authors:
Hun Young Kim; Jian-Yuan Li; Kyungsoo Oh
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-12-3
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Dec 
Date Detail:
Created Date:  2012-12-3     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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