Reactions of Br80 (18 min) Produced by Isomeric Transition of Br80m (4.58 hr) with Benzene and Methylated Benzenes

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Abstract
The reactions of benzene, toluene, para‐ and ortho‐xylene, and mesitylene with Br80 as a result of isomeric transition have been studied. It was found that the reactions were complex. The substitution reaction was accompanied by condensation reactions. Evidence was found that organic bromides with boiling points higher than bromobenzene were formed in appreciable yields. Hydrolysis experiments indicated that both primary and secondary bromides were included in these high boiling compounds. Scavenger experiments indicated that the substitution reactions were proceeding in the main through fast bromine atom reactions. No evidence was obtained that any appreciable amounts of the substitution reactions were proceeding through a positive bromine ion mechanism.