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Some time ago one of us2 called attention to the fact that certain compounds containing bromine or iodine in the benzene ring could undergo hydrolysis in such a way that the halogen was replaced by hydrogen, while the solution acquired oxidizing properties evidenced by the liberation of free halogen, or by the formation of more highly halogenated derivatives. Such behavior might be said to constitute the experimental definition of what is here meant by a positive3 halogen in organic combination.In the cases previously cited, the halogen which reacted in this manner was always ortho or para to an amino or hydroxyl group. As these radicals are among the most strongly negative recognized by advocates of modern theories of polar valence4 as applied to organic compounds, the results are well in accord with those to be deduced from the electronic structure of benzene as depicted by Stieglitz6 or from the theory of induced alternations in polarity.6,7 As a further consequence of these theories

This type of reaction represents a novel characteristic of this well-known catalyst. Nickel also catalyzes the cleavage of dibutyl zinc and diphenylmagnesium with the formation of butane and benzene, respectively.

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