Reactions of halogenoaliphatic acids with free radicals in aqueous solution. Part II. Reactions with aliphatic free radicals

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Abstract
Dehalogenation of halogenoaliphatic compounds by aliphatic free radicals was investigated. The reactivity of the radicals studied followed the sequence BrCH2·CH·OH ClCH2·CH·OH > (CH3)2C·OH > CH3·CH·OH > CH2·OH CBr2·CO2H > CH3·CBr·CO2H > BrCH·CO2H CH3·CH·CO2H CH2·CO2H. The last two radicals do not induce any dehalogenation. The reactivity of the substrates toward the radicals increases in the order ClCH2·CH2·OH < ClCH2·CO2H < BrCH2·CO2H < CBr3·CO2H. The results indicate a charge-transfer mechanism in these reactions rather than halogen abstraction.