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Direct Observation of an Imidoylnitrene: Photochemical Formation of PhC(=NMe)−N and Me−N from 1‐Methyl‐5‐phenyltetrazole
Author(s) -
Abe Manabu,
Bégué Didier,
SantosSilva Hugo,
Dargelos Alain,
Wentrup Curt
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201712689
Subject(s) - photodissociation , chemistry , photochemistry , excited state , irradiation , spectroscopy , carbodiimide , organic chemistry , physics , atomic physics , quantum mechanics , nuclear physics
The imidoylnitrene 8 , N ‐methyl‐ C ‐phenylimidoylnitrene, has been generated by laser photolysis of 1‐methyl‐5‐phenyltetrazole 6 at 5 K and characterized by its ESR spectrum (| D / hc |=0.9602, | E / hc |=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 : | D / hc |=0.123 cm −1 , E / hc =0.0065 cm −1 , 11 : | D / hc |=0.126 cm −1 , | E / hc |=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.