| Reactivity of halo(pyridinium)carbenes. | |
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MedLine Citation:
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PMID: 19904904 Owner: NLM Status: In-Process |
Abstract/OtherAbstract:
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The reactivity of chloro- and fluoro(N-methyl-3-pyridinium)carbenes was examined by laser flash photolysis, where the halo(pyridinium)carbenes formed ylides with pyridine, acetonitrile, and acetone. Although the halo(pyridinium)carbenes reacted within the time of the laser pulse, their relative reactivities with a series of alkenes could be obtained from quenching experiments by using carbene-pyridine ylides. Their relative order of reactivity with the alkenes and their poor overall selectivity showed that the halo(pyridinium)carbenes are strongly reactive electrophilic species. Computational studies demonstrated that the alkene (HOMO)-carbene (LUMO) interaction is predominant in halo(pyridinium)carbene-alkene reactions, supporting the electrophilic nature of these species. |
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Authors:
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Reinaldo Moya-Barrios; Benjamin M Fregeau; Frances L Cozens |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 74 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2009 Dec |
Date Detail:
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Created Date: 2009-12-02 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 9126-31 Citation Subset: - |
Affiliation:
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Department of Chemistry, Dalhousie University, Halifax, Nova Scotia B3H 4J3, Canada. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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