Electrooxidation of bromoalkanes on platinum in liquid hydrogen fluoride. Selective displacement of bromine by fluorine | Health & Environmental Research Online (HERO)

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Citation
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HERO ID

5491837

Reference Type

Journal Article

Title

Electrooxidation of bromoalkanes on platinum in liquid hydrogen fluoride. Selective displacement of bromine by fluorine

Author(s)

Badoz-Lambling, J; Thiebault, A; Oliva, P

Year

1979

Is Peer Reviewed?

Yes

Journal

Electrochimica Acta
ISSN: 0013-4686

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

Location

OXFORD

Volume

Issue

Page Numbers

1029-1037

Web of Science Id

WOS:A1979HN61300015

URL

http://www.sciencedirect.com/science/article/pii/0013468679871029
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Abstract

Carbon—bromine bond cleavage was investigated in HF as a privileged route to the formation of electrophilic carbon ions and subsequent obtention of alkyl fluorides. Nucleophilic attack of fluoride ions on electrochemically generated radical cations, R—Br+, or carbenium ions, R+, proved selective and quantitative in the case of bromomethane, 1,2-dibromoethane, 1,2-dibromopropane, 1,3-dibromo propane and 1,2,3-tribromopropane. For bromoethane, 1-(or 2-)bromopropane, 1-(or 2-)bromobutane, 1-bromo-2-methyl propane and 1-bromo-3-methyl butane, the observed lack of halogenation selectivity is discussed in terms of radical side reactions.