PHENYLARSINES WITH PHENYLHALOARSINES 3353derivative and the aniline, while in the cold, stannous chloride in the presence of hydrochloric acid gave the aniline along with the unchanged hydrazobenzene.The tables indicate the conditions of attempted rearrangement and the products isolated.
1.
SummaryA study of the properties of sym.-hexabromohydrazobenzene has shown that it cannot be responsible for the formation of a pentabromoquinoneimine obtained by the oxidation of sym.-tribromoaniline in acid solution with chromic anhydride. It is, therefore, probable that N analogs of the type A and type B radicals postulated in the oxidation of sym.-halogenated phenols play the important role.2 . Sym.-hexabromohydrazobenzene and 2,4,2',4'-tetrabromohydrazobenzene do not undergo the benzidine type of rearrangement. Instead they oxidize and reduce to the corresponding azo and aniline derivatives in the presence of a mineral acid without a reducing agent; in the presence of a reducing agent they are split to the anilines.
3.A method for the preparation of azo compounds is described.
MINNEAPOLIS, MINNESOTASeveral years ago it was announced by Steinkopf and Smie2 that phenyldichloroarsine and diphenylarsine react to form triphenylchlorodiarsyl. C&AsC12 + ( C&)~ASH = C&( Cl)As-As( CsHs)2 + HC1 Since we wished to prepare triphenylhydroxydiarsyl,2a hydrolysis of the corresponding chloro compound suggested itself as a preparative procedure. Phenyldichloroarsine and diphenylarsine were allowed to react in the proportions used by the above-mentioned investigators but instead of triphenylchlorodiarsyl, arsenobenzene and diphenylchloroarsine were obtained in yields which correspond closely to those calculated from equation A.3
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