Synthesis of Stable 1,2-Diazocines, 4,7-Disubstituted 3,8-Diaryl-1,2-diazacycloocta-2,4,6,8-tetraenes, and Their Thermolysis

Abstract

Abstract Stable 1,2-diazocines, 3,8-diaryl-4,6-dichloro-1,2-diazacycloocta-2,4,6,8-tetraenes, were prepared via a chlorination–dehydrochlorination sequence starting from readily-available 3,8-diaryl-1,2-diazacycloocta-2,8-dienes. When reacted with metal carboxylates in benzene under reflux, the dichloro-1,2-diazocines were converted into stable 4-acyloxy- and/or 4,7-bis(acyloxy)-1,2-diazocines. On the thermolysis in toluene under reflux, all the diazocines gave only pyridine derivatives with extrusion of the corresponding benzonitriles. The thermal behavior of the diazocines are also discussed.