Abstract
The main features of the peroxidation of 4-chloroaniline are the production of 2-amino-5-(4-chloroanilino-)benzoquinone-di-4-chloroanil in high yield and the elimination of chloride ion. Two intermediates, (N-(4-chlorophenyl-)p-phenylenediamine and 4-chloro-N2-(4-chlorophenyl-)o-phenylenediamine), have been proposed; and it has been shown that while the former may be an intermediate the latter is not: the latter gives rise to 2-amino-5-chlorobenzoquinone-di-4-chloroanil, a compound which we have detected in the 4-chloroaniline oxidation products. This compound is stable to the conditions of oxidation and is not the precursor of the main oxidation product.The relative yields of the oxidation products have been shown to depend on the initial concentration of 4-chloroaniline.
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