Boron trichloride adducts of some primary aromatic amines. Their constitution and behaviour in acetonitrile

Abstract

Adducts of boron trichloride with p-nitroaniline and its N-deuteriated analogue, m-nitroaniline, p-chloroaniline, and p-iodoaniline have been made, and shown by spectroscopic methods to be σ-complexes, with the aminoprotons retaining their identity. In acetonitrile these complexes undergo exchange processes, followed by elimination of hydrogen chloride. The reactions were investigated by n.m.r. spectroscopy, and mechanisms are proposed.