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.
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