Photochemical Decomposition of 1-Alkoxy-2-azidophenazines. Addition of Nitrenes to Azides

Article abstract of DOI:10.1021/jo00025a010

The photolysis of 2-azido-1-methoxyphenazine (1a) and its ethoxy homologue (1b) takes an unusual course.It involves the addition of a singlet nitrene or one of its cyclic tautomers to the ground-state azide to form the N-phenazinyl iminoether 9a (from 1a) and a 2-oxazolo<5,4-a>phenazinyl derivative of a quinoxalinylpropenenitrile (10, from both 1a and 1b).Products derived from the triplet nitrene are formed as well.The effects of varying some of the experimental conditions were determined.A mechanism for the photolysis is proposed.