Document Detail


Omega-halonitriles: domino cyclizations to oxa- and carbocyclic nitriles.
MedLine Citation:
PMID:  12737576     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
t-BuOK-induced deprotonation of omega-haloalkylnitriles generates remarkably stable potassiated nitriles. In situ deprotonation and alkylation of omega-chloroalkylnitriles with aldehyde electrophiles trigger sequential nucleophilic-electrophilic alkylations generating substituted tetrahydrofuranyl and tetrahydropyranyl nitriles. Redirecting the cyclization manifold with 5-iodopentanenitrile and a ketone causes a complementary electrophilic-nucleophilic cyclization to the corresponding carbonitrile. Collectively these cyclizations provide rapid assembly of five- and six-membered oxa- and carbocyclic nitriles demonstrating the utility of omega-halonitriles in domino alkylations.
Authors:
Fraser F Fleming; Venugopal Gudipati; Omar W Steward
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  68     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2003 May 
Date Detail:
Created Date:  2003-05-09     Completed Date:  2003-12-23     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3943-6     Citation Subset:  IM    
Affiliation:
Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, Pennsylvania 15282-1530, USA. flemingf@duq.edu
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MeSH Terms
Descriptor/Qualifier:
Alkylation
Catalysis
Chemistry, Organic / methods*
Cyclization
Hydrocarbons, Halogenated* / analysis,  chemical synthesis,  chemistry
Indicators and Reagents
Magnetic Resonance Spectroscopy
Molecular Structure
Nitriles* / analysis,  chemical synthesis,  chemistry
Potassium / chemistry
Stereoisomerism
Chemical
Reg. No./Substance:
0/Hydrocarbons, Halogenated; 0/Indicators and Reagents; 0/Nitriles; 7440-09-7/Potassium

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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