Abstract
The formation and fate of benzylic bromides during the cobalt acetate bromide catalyzed oxidation of toluene and 4-chlorotoluene were investigated in carboxylic acid solvents. The rate of formation of benzylic bromides depends on the substrate and catalyst concentrations while the conversion of ionic bromide to benzylic bromides is strongly influenced by the type of solvent and the presence of nucleophilic ligands and metal co-catalysts. The observed effects are best explained in terms of a chain carrier comprising both cobalt acetate and bromide. Oxidation of benzylic bromides under the reaction conditions results in the formation of benzal bromides, benzaldehydes, benzoic acid and molecular bromine. An electron transfer process is proposed to explain the oxidation of benzylic bromides.
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