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

    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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