- 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
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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 to phthalide-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.Keywords - cyanogen chloride; 1-naphthol; 4-phenylimidazole; histidine; chloramine; hypochlorous acid
- Ohya, Takeshi,Kanno, Saburo
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p. 4095 - 4102
(2007/10/02)
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