Formation of cyanide ion or cyanogen chloride through the cleavage of aromatic rings by nitrous acid or chlorine. IX. On the reactions of chlorinated, nitrated, carboxylated or methylated benzene derivatives with hypochlorous acid in the presence of ammonium ion

Abstract

Chlorinated, nitrated, carboxylated or methylated benzenes, phenols and anilines reacted with chloramine to give cyanogen chloride, independently of the positions and the numbers of the substituents. Among these compounds, 2,4,6-trichlorophenol afforded cyanogen chloride in a relatively high yield of 13.3%, and the intermediates in the reaction were 2,6-dichloro-1,4-benzoquinone-4-(N-chloro)imine and 4,6-dichloro-1,2-benzoquinone-2-(N-chloro)-imine, of which the latter was the main intermediate.