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 language | English |
|---|---|
| Pages (from-to) | 2537-2544 |
| Number of pages | 8 |
| Journal | Journal of the Chemical Society - Perkin Transactions 1 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 1990 |
| Externally published | Yes |
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Dive into the research topics of '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'. Together they form a unique fingerprint.Cite this
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