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

被引：15

作者：

Battiste, MA ^{[1
]}

Tian, F ^{[1
]}

Baker, JM ^{[1
]}

Bautista, O ^{[1
]}

Villalobos, J ^{[1
]}

Dolbier, WR ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2003年 / 119卷 / 01期

关键词：

(2,2-difluorocyclopropyl)methyl radical and cation; solvolysis; kinetics; DFT calculations;

D O I：

10.1016/S0022-1139(02)00248-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The rate constants for acetolysis of (2,2-difluorocyclopropyl)methyl tosylate, and (2,2-difluoro-3-methylcyclopropyl)methyl tosylate at 92degreesC and of 1-(2,2-difluorocyclopropyl)ethyl tosylate at 42degreesC 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)mithyl systems as mechanistic probes. (C) 2002 Elsevier Science B.V. All rights reserved.

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页码：39 / 51

页数：13

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