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Mechanistic study demonstrates an elimination-addition pathway in halobenzenes treated with metallic amides, indicating the presence of a benzyne intermediate.
An elimination-addition mechanism, probably involving a "benzyne" intermediate, has been established for the rearrangements which often occur in the conversion of non-activated aryl halides to arylamines with metallic amides. The evidence for the "benzyne" intermediate was obtained through ^(14)C-tracer studies of rearrangements with halobenzenes and experiments designed to determine the role of the hydrogen atom located ortho to the displaced halogen atom.
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Roberts et al. (1956) studied this question.
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