Reactivity and regiochemical behavior in the solvolysis reactions of (2,2-difluorocyclopropyl)methyl tosylates

Graphic The rate constants for acetolysis of (2,2-difluorocyclopropyl)methyl tosylate, and (2,2-difluoro-3-methylcyclopropyl)methyl tosylate at 92 °C and of 1-(2,2-difluorocyclopropyl)ethyl tosylate at 42 °C are reported and the reactivities and regiochemistries of ring opening of these systems are...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2003, Vol.119 (1), p.39-51
Main Authors: Battiste, Merle A, Tian, Feng, Baker, John M, Bautista, Olivia, Villalobos, Janette, Dolbier, William R
Format: Article
Language:English
Subjects:
(2,2-Difluorocyclopropyl)methyl radical and cation
DFT calculations
Kinetics
Solvolysis
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Summary:Graphic The rate constants for acetolysis of (2,2-difluorocyclopropyl)methyl tosylate, and (2,2-difluoro-3-methylcyclopropyl)methyl tosylate at 92 °C and of 1-(2,2-difluorocyclopropyl)ethyl tosylate at 42 °C are reported and the reactivities and regiochemistries of ring opening of these systems are discussed and compared with expectations based on computational results. The results are discussed in terms of the use of (2,2-difluorocyclopropyl)methyl systems as mechanistic probes.
ISSN:0022-1139
1873-3328
DOI:10.1016/S0022-1139(02)00248-8