Organophosphorus chemistry. Part XIII. The reaction of phosphorus trichloride with primary aromatic amines

Abstract

The reaction of an excess of phosphorus trichloride with primary aromatic amines yields aryliminobisdichlorophosphines at ambient temperatures and the corresponding 1,3-diaryl-2,4-dichloro-1,3,2,4-diazadiphosphetidines at 100–120°. Dichloro-(4-nitroanilino)phosphine. isolated from the reaction of 4-nitroaniline and phosphorus trichloride, is converted by an excess of phosphorus trichloride in the presence of pyridine into 4-nitrophenyliminobisdichlorophosphine. Phosphorus trichloride reacts with hexamethyl-N-phenyldisilazane to give 2,4-dichloro-1,3-diphenyl-1,3,2,4-diazadiphosphetidine. Phenyliminobisdichlorophosphine reacts with hexamethyl-N-phenyldisilazane to give 2,4-dichloro-1,3-diphenyl-1,3,2,4-diazadiphosphetidine and with dimethylaminotrimethylsilane to give 2,4-bisdimethylamino-1,3-diphenyl-1,3,2,4-diazadiphosphetidine. ¹H N.m.r. and mass spectroscopic data for some of these compounds are discussed.