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The formation of anisóle from the reactions of various lithium dialkylamides with o-bromoanisole was investigated. It was established that the dialkylamide ion is concomitantly oxidized as the aryl halide is reduced. Thus lithium benzylmethylamide when treated with o-bromoanisole was oxidized to 2,5-diphenylpyrazine; lithium dibenzylamide to 2,3,5,6tetraphenylpyrazine; and lithium 6¿s-(p-methoxybenzyl)amide to 2,3,5,6-tetra-(p-methoxyphenyl)pyrazine.That the initial oxidation product might be an imine was demonstrated when lithium benzylmethylamide reacted with Nbenzilidinemethylamine to give 2,5-diphenylpyrazine. Also lithium dibenzylamide when treated with N-benzilidinebenzylamine gave 2,3,5,6-tetraphenylpyrazine.A possible reaction mechanism which is consistent with these findings is presented.

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