A new fused tricyclic tetra-aza[4.3.3.01,6]dodecene system: substituted 3,3a,4,5,6,6a-hexahydropyrrolo[2,3-d]-1,2,3-triazoles from the reaction of acrylonitrile with cis-1,2-bis(areneazo)ethylenes and a re-assessement of 1,3-cycloaddition products

Abstract

The thermal reaction of cis-1,2-bis(areneazo) ethylenes with acrylonitrile gave substituted 3,3a,4,5,6,6a-hexahydropyrrolo[2,3-d]-1,2,3-triazoles with a saturated bridgehead which, when fused to a cyclohexyl ring, constituted a tricyclic tetra-azadodecene structure; these products could not arise directly from 1,3-dipolar cycloadditions.