Azapropellanes: new fused tetra-azatriazolo[n.3.3.01,x]-dodecenes and tridecenes. Substituted 3,3a,4,5,6,6a-hexahydropyrrolo[2,3-d]-1,2,3-triazoles from a general tandem cycloaddition–rearrangement reaction of 1,2,3-triazolium imides with substituted alkenes: kinetics and mechanism: azolium 1,3-dipoles. Part 3

Abstract

Reactions of substituted 1,2,3-triazolium-1-imide 1,3-dipoles with a range of substituted alkene and alkyne dipolarophiles gave rise to derivatives of the new ring systems hexahydropyrrolo[2,3-d]-1,2,3-triazoles and the azapropellanes tetra-aza-tricyclo[5.3.3.0^1,7]tridecenes and -tricyclo[4.3.3.0^1,6]dodecenes. The reactions, which are regio- and stereo-specific, are shown to be tandem 1,3-dipolar (endo) cycloadditions and sigmatropic rearrangements. X-Ray crystal structures of 6exo-ethoxycarbonyl-2,3a,4,6a-tetraphenyl-3,3a,4,5,6,6a-hexahydropyrrolo[2,3-d]-1,2,3-triazol-2-ium-3-ide (9a) and 12exo-cyano-8,10-diphenyl-7,8,9,10-tetra-azatricyclo[4.3.3.0^1,6]dodec-7-en-8-ium-9-ide (4a; m= 2) are reported.