Stereoselective Formation of Linear AZA-Triquinanes by Three Consecutive Radical Ring Closures

  • Lucien Stella
  • Doug Boate
  • Eric Guittet
Part of the NATO ASI Series book series (ASIC, volume 260)


Treatment of the trienyl N-chloroamine 5 with titanium trichloride affords regio- and stereoselectively, as the major product (nearly half of the overall yield) the 8-aza-4-anti-chloromethyl-cis, syn, cis tricyclo (6, 3, 0, 0 2,6) undecane 10d by serial homolytic cyclisations.


Tetrahedron Letter Bicyclic Compound Medium Pressure Liquid Chromatography Titanium Trichloride Bridgehead Carbon 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. (1).
    For recent reviews, see: (a) Beckwith, A.L.J.; Ingold, K.U. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980, pp 162–283.Google Scholar
  2. (1)(b).
    Surzur, J-M. In Reactive Intermediates; Abramovitch, R.A., Ed.; Plenum: New York, 1981; vol. 2, Chapter 3.Google Scholar
  3. (1)(c).
    Beckwith, A.L.J., Tetrahedron, 1981, 37, 3073 and references thereinCrossRefGoogle Scholar
  4. (1)(d).
    Griller, D.; Ingold, K.U. Acc. Chem. Res. 1980,:13, 317.CrossRefGoogle Scholar
  5. (2)(a).
    Hart, D.J. Science, 1984, 223, 883.CrossRefGoogle Scholar
  6. (2)(b).
    Stork, G.; Mook, Jr. R. J. Am. Chem. Soc. 1987, 109, 2829.CrossRefGoogle Scholar
  7. (2)(c).
    Curran, D.P.; Chen, M.-H. J. Am. Chem. Soc. 1987, 109, 6558.CrossRefGoogle Scholar
  8. (2)(d).
    Clive, D.L.J.; Boivin, T.L.B.; Angoh, A.G. J. Org. Chem. 1987, 52, 4943.CrossRefGoogle Scholar
  9. (2)(e).
    Padwa, A.; Nimmergern, H.; Wong, G.S.K., J. Org. Chem., 1985, 50, 5620.CrossRefGoogle Scholar
  10. (3).
    Stella, L. Angew. Chem. Int. Ed. Engl. 1983, 22, 337.CrossRefGoogle Scholar
  11. (4)(a).
    Stella, L., Raynier, B.; Surzur, J.M. Tetrahedron, 1981, 37, 2843.CrossRefGoogle Scholar
  12. (4)(b).
    Surzur, J.M.; Stella, L. Tetrahedron Letters, 1974, 2191.Google Scholar
  13. (5).
    Chastanet, J.; Roussi, G. Heterocycles, 1985, 23, 653.CrossRefGoogle Scholar
  14. (6).
    Jones, T.H.; Blum, M.S.; Fales, H.M.; Thompson, C.R. J. Org. Chem. 1980, 45, 4778.CrossRefGoogle Scholar
  15. (7).
    Beckwith, A.L.J.; Easton, C.J.; Serelis, A.K. J. Chem. Soc., Chem. Commun. 1980, 482.Google Scholar
  16. (8).
    Hawthorne, D.G.; Johns, S.R.; Willing, R.I. Aust. J. Chem. 1976, 29, 315.CrossRefGoogle Scholar
  17. (9).
    Beckwith, A.L.J.; Philipon, G.; Serelis, A.K. Tetrahedron letters, 1981, 22, 2811.CrossRefGoogle Scholar
  18. (10)a).
    Beckwith, A.L.J.; Hawthorne, D.G.; Solomon, D.H. Aust. J. Chem. 1976, 29, 995CrossRefGoogle Scholar
  19. (10)b).
    Corfield, G.C. Chem. Soc. Rev. 1972, 1, 523CrossRefGoogle Scholar
  20. (10)c).
    Solomon, D.H., J. Macromol. Sci. 1975, A9, 97.Google Scholar

Copyright information

© Kluwer Academic Publishers 1989

Authors and Affiliations

  • Lucien Stella
    • 1
  • Doug Boate
    • 1
  • Eric Guittet
    • 2
  1. 1.Laboratoire de Chimie Organique BUniversité d’Aix-Marseille 3Marseille Cedex 13France
  2. 2.Institut de Chimie des Substances NaturellesCNRSGif sur YvetteFrance

Personalised recommendations