Photochemical decomposition of 1-alkoxy-2-azidophenazines. Addition of nitrenes to azides
作者:A. Albini、G. Bettinetti、G. Minoli
DOI:10.1021/jo00025a010
日期:1991.12
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.
Inter- and intramolecular reactions of nitrenes and their cyclic isomers in the photodecomposition of some substituted 2-azidophenazines