Nucleophilic displacement in polyhalogenoaromatic compounds. Part 6. Kinetics of methoxydefluorination of polybromofluorobenzenes
Abstract
Rates of displacement of fluorine from a number of polybromofluorobenzenes by methanolic sodium methoxide have been measured at 323.2 K. The effects of bromine substituents, whether measured by substituent rate factors or by the two-term process described earlier, fall in a regular sequence of halogen effects, from fluorine to iodine. The poorer agreement between calculated and experimental figures for the heavier halogens must reflect other unconsidered factors perhaps arising from crowding or from mutual interaction of the substituents.
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