Reactions of 3-aryl-1-(tetrazol-5′-yl)triazenes with some electrophiles: Mercury derivatives and fragmentations: A new route to aryl diazocyanides

Treatment of 3-aryl-1-(tetrazol-5′-yl)triazenes (4) with lead tetra-acetate resulted in a fragmentation to aryl diazocyanides. The triazenes (4) and their monomethyl derivatives when treated with mercuric acetate and phenylmercury hydroxide gave stable mercuri compounds with mercury bonded at N-3 and the tetrazole N-2′. The reaction of the triazenes with acetic anhydride resulted in acetylation of the triazene unit with fragmentation to aryl diazonium ions and 5-acetamidotetrazoles. These reactions are discussed and the ¹³C n.m.r. spectra of the products are analysed.