Direct Observation of an Imidoylnitrene: Photochemical Formation of PhC(=NMe)-N and Me-N from 1-Methyl-5-phenyltetrazole

The imidoylnitrene 8, N-methyl-C-phenylimidoylnitrene, has been generated by laser photolysis of 1-methyl-5-phenyltetrazole 6 at 5K and characterized by its ESR spectrum (vertical bar D/hc vertical bar=0.9602, vertical bar E/hc vertical bar=0.0144 cm(-1)). In addition, the triplet excited states of 6 and of 2-methyl-5-phenyltetrazole 11 were also observed by ESR spectroscopy in the 5 K matrices (6:vertical bar|D/hc vertical bar=0.123 cm(-1), E/hc=0.0065 cm(-1), 11: vertical bar D/hc vertical bar=0.126 cm(-1), vertical bar E/hc vertical bar=0.0056 cm(-1)). The imidoylnitrene 8 is unstable both thermally (disappearing at 80 K) and photochemically (disappearing on continued irradiation at 266 nm). Methyl(phenyl)carbodiimide is the end product of photolysis.