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

  • Richard N. Butler
  • , Ann M. Evans
  • , Ann M. Gillan
  • , John P. James
  • , Eithne M. McNeela
  • , Desmond Cunningham
  • , Patrick McArdle

Research output: Contribution to a Journal (Peer & Non Peer)Articlepeer-review

22 Citations (Scopus)

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[5.3.3.01,7]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.

Original languageEnglish
Pages (from-to)2537-2544
Number of pages8
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number9
DOIs
Publication statusPublished - 1990
Externally publishedYes

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