Umwandlung von 5H-Dibenz[c.e]azepinen in Phenanthridine über cyclische N-Diazonium-Ionen / Conversion of 5H-Dibenzo[c,e]azepines into Phenanthridines via Cyclic N-Diazonium Ions

Abstract

Abstract The reaction of 6-amino-6,7-dihydro-5H-dibenzo[c,e]azepine, bearing a terminal blocking group, with trifluoracetylnitrite presumably proceeds via cyclic 7-membered N-diazonium ions and mainly leads to the formation of phenanthridine by migration of the aryl group. 5H-Dibenzo[c,e]azepine can be isolated as the minor product and seems to be the result of a hydrogen shift. N ,N′-Azo-6,7-dihydro-5H-dibenzo[c,e]azepine dis-plays an analogous behaviour.