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

Article abstract of DOI:10.1246/bcsj.59.1087

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-2,4-dienes.When reacted with metal caroxylates in benzene under reflux, the dichloro-1,2-diazocines were converted into stable 4-acyloxy- and/or 4,7-is(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.