Characterization and Reactivity of the [N,N-Dimethyl(thioformamidyl)]-9-fluorenyl Cation

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DOIResolve DOI: http://doi.org/10.1021/jo941685m
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TypeArticle
Journal titleJournal Of Organic Chemistry
ISSN00223263
Volume61
Issue20
Pages68056808; # of pages: 4
AbstractThe 9-[N,N-dimethyl(thioformamidyl)]-9-fluorenyl cation was generated under stable ion conditions and characterized by UV/visible and NMR spectroscopy and methanol trapping reactions. The same cation was generated by laser excitation of the appropriate chloride precursor in 2,2,2-trifluoroethanol, and rate constants for nucleophilic quenching by alcohols and several anions were measured. The quenching data for this and other 9-fluorenyl cations demonstrate that the reactivity decreases for 9-substituents in the order H > carbomethoxy > N,N-dimethyl(thioformamidyl), demonstrating that the thioamidyl group imparts substantial kinetic stabilization to an adjacent cationic center. Both steric and electronic factors are suggested to be important in determining this reactivity order.
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AffiliationNational Research Council Canada; NRC Industrial Research Assistance Program; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
Identifier10008226
NPARC number12327463
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Record identifier7a6ba6d5-be5d-463a-aabd-396a858cba5c
Record created2009-09-10
Record modified2016-05-09
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