Photochemistry of fluorophenyl azides in aniline: Asymmetric fluoroazobenzenes by NH singlet nitrene insertion

Several fluorophenyl azides were photolyzed with aniline at room temperature. Only pentafluoro and 2,6-difluorophenyl azides gave asymmetrical fluoroazobenzenes as the major products. These products were generated by singlet NH insertion reaction with aniline followed by oxidation of the resulting aromatic hydrazine.