Some alternatives to the “benzyne” (elimination-addition) mechanism for aminations of non-activated halobenzenes have been disproved by the finding that the amination of iodobenzene-1-^(14)C-2,4,6^(-2)H_3 gives the same extent of ^(14)C rearrangement in the resulting aniline as does iodobenzene-1-^(14)C. The intermediacy of substituted benzynes in non-rearranging aminations of 3-substituted halobenzenes has been confirmed by a study of the hydrogen-deuterium kinetic isotope effect in reactions of 3-bromoanisole-2,4,6-^2H_3.
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Panar et al. (1960) studied this question.