The kinetic and thermodynamic influence of fluorine versus methyl substituents in methylenecyclopropane rearrangements

A comprehensive review of the kinetic and thermodynamic influences of methyl and fluorine substituents on the methylenecyclopropane rearrangement is presented. In spite of a superficial similarity of the overall influence of these two substituents, methyl's effect derives largely from the incre...

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Bibliographic Details
Published in:Journal of fluorine chemistry 1996-03, Vol.77 (1), p.31-37
Main Authors: Dolbier, William R., Burkholder, Conrad R., Lucia Chaves, Alba, Green, Astor
Format: Article
Language:English
Subjects:
Fluorine substituents
Kinetic influence
Methyl substituents
Methylene cyclopropane rearrangements
NMR spectroscopy
Thermodynamic influence
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Summary:A comprehensive review of the kinetic and thermodynamic influences of methyl and fluorine substituents on the methylenecyclopropane rearrangement is presented. In spite of a superficial similarity of the overall influence of these two substituents, methyl's effect derives largely from the incremental nature of its radical- and alkene-stabilizing, and steric impact, while fluorine's effect derives from its large and non-incremental influence on the strain of cyclopropane coupled with its similarly variable effect on the stability of alkenes and free radicals.
ISSN:0022-1139
1873-3328
DOI:10.1016/0022-1139(95)00376-2