The Chlorination of aromatic compounds by N-chlorocompounds

Abstract

The chlorination by N-chloromorpholine of aromatic compounds with a wide range of reactivity has been investigated from a kinetic point of view. The mechanism in the presence of perchloric acid has been shown to involve direct reaction between the N-chloromorpholinium ion and the aromatic compound. In hydrochloric acid, however, this mechanism changes with compounds of lower reactivity to one involving molecular chlorine as an intermediate. An investigation of the reaction between N-chloropiperidine and phenol has also been carried out and it has been found that in the presence of perchloric acid, direct chlorination by the N-chloropiperidinium ion occurs. This experimental data is used to provide a theoretical explanation for the kinetic differences between chlorination by N-chloroamines and N-chloroamides and suggestions for further experimental work are given.