Document Detail


First kinetic discrimination between carbon and oxygen reactivity of enols.
MedLine Citation:
PMID:  18844419     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
Nitrosation of enols shows a well-differentiated behavior depending on whether the reaction proceeds through the carbon (nucleophilic catalysis is observed) or the oxygen atom (general acid-base catalysis is observed). This is due to the different operating mechanisms for C- and O-nitrosation. Nitrosation of acetylacetone (AcAc) shows a simultaneous nucleophilic and acid-base catalysis. This simultaneous catalysis constitutes the first kinetic evidence of two independent reactions on the carbon and oxygen atom of an enol. The following kinetic study allows us to determine the rate constants for both reaction pathways. A similar reactivity of the nucleophilic centers with the nitrosonium ion is observed.
Authors:
Luis García-Río; Juan C Mejuto; Mercedes Parajó; Moisés Pérez-Lorenzo
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Publication Detail:
Type:  Journal Article     Date:  2008-10-10
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  73     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2008 Nov 
Date Detail:
Created Date:  2008-11-03     Completed Date:  2009-01-09     Revised Date:  2013-02-26    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  8198-205     Citation Subset:  -    
Affiliation:
Departamento de Química Física, Facultade de Química, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain. qflgr3cn@usc.es
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Comment In:
Org Biomol Chem. 2013 Feb 14;11(6):1065-70   [PMID:  23282986 ]
Org Biomol Chem. 2013 Feb 14;11(6):1059-64   [PMID:  23288218 ]

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