Re-examination of the reaction of β-naphthol with trans-p-nitrobenzene-diazocyanide: a novel fission of the azo double bond
Abstract
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.