Treatment of β-naphthol with trans-p-nitrobenzenediazocyanide has been shown to give 1-(p-nitrophenyl)-iminonaphthalen-2(1H)-one and N1-cyano-p-nitrophenylazoformamidine. The ready fission of the azo double bond is explained by a mechanism involving electrophilic attack on β-naphthol by the diazocyanide followed by elimination of cyanamide.
Y. Kikuchi, T. Mitsuhashi, O. Simamura and M. Yoshida, J. Chem. Soc. C, 1971, 2074 DOI: 10.1039/J39710002074
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