Functionalization of Phenyl Rings by Imidoylnitrenes. 2. Cycloaddition or Electrophilic Aromatic Substititution

@inproceedings{Dabbagh1996FunctionalizationOP,
  title={Functionalization of Phenyl Rings by Imidoylnitrenes. 2. Cycloaddition or Electrophilic Aromatic Substititution},
  author={Hossein Abdoul Dabbagh and Saied Ghaelee},
  year={1996}
}
The thermal decomposition of N‘-[(cyanoaryl)oxy]imidoyl azides with various substituted benzenes (OCH3, NHCOCH3, C(CH3)3, p-xylene, CH3, H, Cl, CO2CH3, NO2) has been studied in detail. With electron-rich aromatic nuclei, the addition of a nitrene yields a benzenonium ion (3) intermediate. Benzaziridine (1) and/or 3 intermediate is formed from benzene. Electron-poor aromatic nuclei generated only intermediate 1, in which no benzenonium diradical is formed. Intermediate 3 is stabilized by… CONTINUE READING