Arranging coordination sites around cyclotriveratrylene

  • Jennifer A. Wytko
  • Jean Weiss
General Papers

Abstract

This article describes the attachement of coordination sites around a rigid matrix: cyclotriveratrylene (CTV). The synthetic approaches leading to these new ligands possessing pyridines and bipyridines as coordinating sites are discussed and full synthetic details are given. One expanded CTV derivative bearing three 3-pyridyl groups has been characterized by X-ray crystallography and the structure shows that the conformation adopted by the CTV matrix is appropriate for the coordination of transition metals, and inclusion of a range of molecules in the hydrophobic pocket.

Key words

Cyclotriveratrylene cavities pyridines 2,2′-bipyridine 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.(a)
    Forreviews see: D. J. Cram:Angew. Chem. Int. Ed. Engl. 27, 1009 (1988);Google Scholar
  2. 1.(b)
    F. N. Diederich:Angew. Chem. Int. Ed. Engl. 27, 362 (1988);Google Scholar
  3. 1.(c)
    J. M. Lehn:Angew. Chem. Int. Ed. Engl. 27, 89 (1988);Google Scholar
  4. 1.(d)
    J. Rebek Jr.:Angew. Chem. Int. Ed. Engl. 29, 245 (1990);Google Scholar
  5. 1.(e)
    D. J. Cram:Nature 356, 29 (1992).Google Scholar
  6. 2.
    E. Tsuchida and H. Nishide:Top. Curr. Chem. 132, 63 (1986).Google Scholar
  7. 3.
    F. P. Schmidtchen:Top. Curr. Chem. 132, 63 (1986) and references therein.Google Scholar
  8. 4.
    D. H. Busch and N. A. Stephenson:J. Incl. Phenom. 7, 137 (1989).Google Scholar
  9. 5.
    R. Breslow, J. W. Canary, M. Varney, S. T. Waddle, and D. Young:J. Am. Chem. Soc. 112, 5212 (1990).Google Scholar
  10. 6.
    Y. Kuroda, T. Hiroshige and H. Ogoshi:J. Chem. Soc., Chem. Commun. 1594 (1990).Google Scholar
  11. 7.
    M. I. Rosenthal and A. W. Czarnick:J. Incl. Phenom. 10, 119 (1991).Google Scholar
  12. 8.
    H. J. Schneider and F. Xiao:J. Chem. Soc., Perkin Trans. 2, 387 (1992).Google Scholar
  13. 9.
    R. Fornasier, E. Scarpa, P. Scrimin, P. Tecilla, and U. Tonnelato:J. Incl. Phenom. 14, 205 (1992).Google Scholar
  14. 10.
    D. R. Benson, R. Valentekovitch, S. W. Tam, and F. Diederich:Helv. Chim. Acta 76, 2034 (1993) and references therein.Google Scholar
  15. 11.
    S. W. Tam-Chang, L. Jimenez, and F. Diederich:Helv. Chim. Acta 76, 2616 (1993).Google Scholar
  16. 12.
    C. D. Gutsche: inCalixarenes, J. F. Stoddart (Ed.), Monographs in Supramolecular Chemistry, The Royal Society of Chemistry, Cambridge (1989).Google Scholar
  17. 13.
    J. Vicens and V. Böhmer: inCalixarenes: A Versatile Class of Macrocyclic Compounds, Kluwer Academic Publishers, Dordrecht, Holland (1991).Google Scholar
  18. 14.
    R. Ungaro and A. Pochini: inFrontiers in Supramolecular Organic Chemistry and Photochemistry, H. J. Schneider and H. Dürr (Eds.), VCH, Weinheim (1991).Google Scholar
  19. 15.
    K. Frensch and F. Vögtle:J. Lieb. Ann. Chem. 2121 (1979).Google Scholar
  20. 16.
    S. Pappalardo, L. Giunta, M. Foti, G. Ferguson, J. F. Gallagher, and B. Kaitner:J. Org. Chem. 57, 2611 (1992).Google Scholar
  21. 17.
    F. Bottino, L. Giunta, and S. Pappalardo:J. Org. Chem. 54, 5407 (1989).Google Scholar
  22. 18.
    C. D. Gutsche and K. C. Nam:J. Am. Chem. Soc. 110, 6153 (1988).Google Scholar
  23. 19.
    F. Hamada, T. Fukugari, K. Murai, G. W. Orr, and J. L. Atwood:J. Incl. Phenom. 10, 57 (1991).Google Scholar
  24. 20.
    D. Matt, C. Loeber, J. Vicens, and Z. Asfari:J. Chem. Soc., Chem. Commun. 604 (1993).Google Scholar
  25. 21.
    C. Floriani, D. Jacoby, A. Chiesi-Villa, and C. Guastini:Angew. Chem. Int. Ed. Engl. 10, 1376 (1989).Google Scholar
  26. 22.
    J. K. Moran and M. Roundhill:Inorg. Chem. 31, 4213 (1992).Google Scholar
  27. 23.
    A. W. Coleman, C. C. Ling, and M. Miocque:Angew. Chem. Int. Ed. Engl. 31, 1381 (1992).Google Scholar
  28. 24.
    Y. Kuroda, M. Ito, T. Sera, and H. Ogoshi:J. Am. Chem. Soc. 115, 7003 (1993).Google Scholar
  29. 25.
    H. K. A. C. Coolen, P. W. N. M. van Leeuwen, and R. J. M. Nolte:Angew. Chem. Int. Ed. Engl. 31, 905 (1992).Google Scholar
  30. 26.
    G. M. Robinson:J. Chem. Soc. 267 (1915).Google Scholar
  31. 27.(a)
    A. S. Lindsey:J. Chem. Soc. 1685 (1965);Google Scholar
  32. 27.(b)
    J. A. Hyatt:J. Org. Chem. 43, 1808 (1978).Google Scholar
  33. 28.
    A. Collet:Tetrahedron 43, 5725 (1987).Google Scholar
  34. 29.
    D. J. Cram, J. Weiss, R. Hegelson, C. B. Knobler, A. E. Dorigo, and K. N. Houk:J. Chem. Soc., Chem. Commun. 407 (1988).Google Scholar
  35. 30.
    J. Canceill, A. Collet, J. Gabard, F. Kotzyba-Hibert, and J. M. Lehn:Helv. Chim. Acta 65, 1894 (1982).Google Scholar
  36. 31.
    E. W. Crandall and L. Harris:Organic. Preparations and Procedures 1 (3), 147 (1969).Google Scholar
  37. 32.(a)
    M. J. Sharp and V. Snieckus:Tetrahedron Lett. 26, 5997 (198);Google Scholar
  38. 32.(b)
    M. J. Sharp, W. Cheng, and V. Snieckus:Tetrahedron Lett. 28, 5093 (1987);Google Scholar
  39. 32.(c)
    W. Cheng and V. Snieckus:Tetrahedron Lett. 28, 5097 (1987);Google Scholar
  40. 32.(d)
    W. J. Gaudino and J. J. Thompson:J. Org. Chem. 49, 5237 (1984).Google Scholar
  41. 33.
    N. Miyaura, T. Yanagi, and T. Suzuki:Synth. Commun. 11, 513 (1981).Google Scholar
  42. 34.
    Y. Yamamoto and A. Yanagi:Chem. Pharm. Bull. 30, 1731 (1982).Google Scholar
  43. 35.
    T. R. Bailey:Tetrahedron Lett. 27, 4407 (1986).Google Scholar
  44. 36.
    A preliminary account of this work has already been published, see: J. A. Wytko and J. Weiss:Tetrahedron Lett. 49, 7261 (1991).Google Scholar
  45. 37.
    D. D. Perrin, W. L. F. Armarego, and D. R. Perrin: inPurification of Laboratory Chemicals, Pergamon, 2nd Edition (1980).Google Scholar
  46. 38.
    J. Wytko, J. Fischer, A. Decian, and J. Weiss:Unpublished Results. Details about crystallographic data of the ligand will be published together with the structure of selected complexes.Google Scholar
  47. 39.
    C. Boudon, J. Wytko, M. Gross, and J. Weiss: Preliminary Communication at theJournées d'Electrochimie, June 7–10, Grenoble, France (1993).Google Scholar
  48. 40.
    G. R. Newkome, V. K. Gupta, and F. R. Fronczek:Inorg. Chem. 22, 171 (1983).Google Scholar

Copyright information

© Kluwer Academic Publishers 1994

Authors and Affiliations

  • Jennifer A. Wytko
    • 1
  • Jean Weiss
    • 1
  1. 1.Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide, URA No. 405 au CNRSUniversité Louis PasteurStrasbourgFrance

Personalised recommendations