Formation of Cyanide Ion or Cyanogen Chloride through the Cleavage of Aromatic Rings by Nitrous Acid or Chlorine. X. Pathway of Cyanogen Chloride Formation in the Reactions of 1-Naphthol and 4-Phenylimidazole with Chloramine

Abstract

The pathway in the formation of cyanogen chloride from the reaction of 1-naphthol (1) and 4-phenylimidazole with chloramine was investigated. The intermediates isolated in the reaction of 1-naphthol (1) with chloramine were N-chloro-1, 2-naphthoquinone 2-imine (2) and o-carboxycinnamonitrile (6), the latter of which, liberating cyanogen chloride, was finally converted tophthalide-3-carboxylic acid (8). The products obtained in the reaction of 4-phenylimidazole (10) with chloramine were benzonitrile (14), benzoylformic acid (22) and benzoic acid (23) besides cyanogen chloride. Cyanogen chloride formed by the reaction of 4-methylimidazole with [¹⁵N]- chloramine was C¹⁴NCl. From these results the pathway of cyanogen chloride formation was elucidated.