Abstract
Abstract Using organic and inorganic Tl salts, the following aromatic brominations were carried out in a CCl4 or HOAc solvent and were found to occur very smoothly; (A) aromatic bromination with TlBr3·4H2O, (B) aromatic bromination with Br2 in the presence of Tl(III) and Tl(I) salts, and (C) the bromination of arylthallium(III) compounds. From a study of the relative rates and selectivities of benzene and toluene, it was deduced that an arylthallium(III) compound was not involved as an intermediate in the A and B reactions, that Tl(III) salts were more effective catalysts than Tl(I) salts for the B bromination, and that the A reaction was essentially identical with the B reaction with the TlBr3·4H2O catalyst. By considering the difference in the catalytic behavior of Tl(III) and Tl(I) salts in the B reaction, probable mechanisms are suggested.
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