Title

Mechanisms for the alkaline hydrolysis of dibromodifluoromethane-alkene adducts to alpha,beta-unsaturated carboxylates

Authors

Authors

S. Elsheimer; J. L. Swanson;J. Gonzalez

Comments

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Abbreviated Journal Title

J. Fluor. Chem.

Keywords

dehydrobromination; hydrolysis; halomethane; Chemistry, Inorganic & Nuclear; Chemistry, Organic

Abstract

Alternative mechanisms for the title reactions are probed. The previously-reported pathway involving double dehydrobromination to a difluorodiene is operative in at least one case, but this route is specifically excluded for systems that cannot dehydrobrominate to dienes yet still yield carboxylates upon alkaline hydrolysis. Although S(N)2, S(N)1, S(RN)1, and monoelimination-addition processes appear formally possible, an S(N)2' mechanism is implicated by studies on model compounds. (C) 2000 Elsevier Science S.A. All rights reserved.

Journal Title

Journal of Fluorine Chemistry

Volume

102

Issue/Number

1-2

Publication Date

1-1-2000

Document Type

Article

Language

English

First Page

3

Last Page

9

WOS Identifier

WOS:000086394100002

ISSN

0022-1139

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