Photolysis of 3,4-Diamidophenyl Azides: Evidence for Azirine Intermediates

Article abstract of DOI:10.1039/c39920001359

Photolysis of the monocyclic aryl azide 3-acetamido-4-trifluoroacetamidophenyl azide, 1a, furnished a long-lived, trapable azirine intermediate, 7, which was in equilibrium with the initially formed nitrene and subsequently rearranged to the didehydroazepine intermediate 5; the data presented demonstrate that mono- and bi-cyclic aryl azides follow the same chemistry, with the substituents controlling the observed product distribution.