THE REACTIONS OF HALOGENATED PHENYLNITROMETHANES WITH TRIETHYL PHOSPHITE

Dibromo and dichloro phenylnitromethanes reacted with triethyl phosphite to yield mainly benzonitrile, ethyl halide, and triethyl phosphate. In addition, the products of molecular rearrangement, N,N-diphenylurea, N-phenylbenzamide, and aniline, were isolated. It is proposed that they arise from the rearrangement of an intermediate, benzonitrile oxide, to phenyl isocyanate. A seventh type of product, chlorobenzalimino diethyl phosphate (9), was obtained from dichlorophenylnitromethane. No rearranged product was isolated from the reaction of triethyl phosphite with the monohalogenated phenylnitromethanes which gave the same main products as their dihalogenated analogues. © 1991.