Effect of base concentration on the rate of the vicarious nucleophilic substitution of hydrogen and on the kinetic isotope effect

Varying concentration of the chloromethyl tolyl sulfone carbanion influences the rate of its VNS reaction with 2-fluoro-4-bromonitrobenzene and changes the mechanistic scheme from thermodynamic to kinetic control. Both primary and secondary kinetic isotope effects are observed and are clearly connec...

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Bibliographic Details
Published in:Tetrahedron letters 1999-10, Vol.40 (42), p.7541-7544
Main Authors: Mąkosza, Mieczyslaw, Lemek, Tadeusz, Kwast, Andrzej
Format: Article
Language:English
Subjects:
isotope effects
mechanisms
nitro compounds
Vicarious nucleophilic substitution
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Summary:Varying concentration of the chloromethyl tolyl sulfone carbanion influences the rate of its VNS reaction with 2-fluoro-4-bromonitrobenzene and changes the mechanistic scheme from thermodynamic to kinetic control. Both primary and secondary kinetic isotope effects are observed and are clearly connected with particular kinetic relations. Dependence of the mechanistic scheme and kinetic isotope effects on the base concentration were observed for the VNS reaction in relation to the fluorine displacement process.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01599-3