Calixpyrroles

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Philip A. Gale, Jonathan L. Sessler and Vladimír Král


Abstract

The calix[4]pyrroles are a class of old but new heterocalixarene analogues that show interesting anion and neutral substrate binding properties. Calix[4]pyrroles are easy to make and functionalize. As such, they have been employed in the production of separation media for anionic and neutral species. Calixpyrroles also provide useful precursors for the generation of novel calixpyridinopyrroles and calixpyridines.


References

  1. A. Baeyer, Ber. Dtsch. Chem. Ges., 1886, 19, 2184 Search PubMed.
  2. A. Baeyer, Ber. Dtsch. Chem. Ges., 1872, 5, 1094 Search PubMed.
  3. P. A. Gale, J. L. Sessler, V. Král and V. Lynch, J. Am. Chem. Soc., 1996, 118, 5140 CrossRef CAS.
  4. M. Dennstedt and J. Zimmerman, Chem. Ber. Dtsch. Ges., 1886, 19, 2189 Search PubMed.
  5. M. Dennstedt and J. Zimmermann, Chem. Ber., 1887, 20, 850 Search PubMed.
  6. M. Dennstedt, Ber. Dtsch. Chem. Ges., 1890, 23, 1370 Search PubMed.
  7. V. V. Chelintzev and B. V. Tronov, J. Russ. Phys. Chem. Soc., 1916, 48, 105 Search PubMed.
  8. V. V. Chelintzev and B. V. Tronov, J. Russ. Phys. Chem. Soc., 1916, 48, 1197 Search PubMed.
  9. P. Rothemund and C. L. Gage, J. Am. Chem. Soc., 1955, 77, 3340 CrossRef.
  10. W. H. Brown, B. J. Hutchinson and M. H. MacKinnon, Can. J. Chem., 1971, 49, 4017 CAS.
  11. V. V. Chelintzev, B. V. Tronov and S. G. Karmanov, J. Russ. Phys. Chem., 1916, 48, 1210 Search PubMed.
  12. J. C. Lalloz and J. M. Lehn, unpublished results reported in Macrocyclic Chemistry, ed. B. Dietrich, P. Viout and J. M. Lehn, VCH, Weinheim, 1993 Search PubMed.
  13. J. C. Lalloz, J. M. Lehn and A. K. Willard, unpublished results reported in Macrocyclic Chemistry, ed. B. Dietrich, P. Viout and J. M. Lehn, VCH, Weinheim, 1993 Search PubMed.
  14. M. Cesario and C. Pascard, unpublished results reported in Macrocyclic Chemistry, ed. B. Dietrich, P. Viout and J. M. Lehn, VCH, Weinheim, 1993 Search PubMed.
  15. C. Floriani, Chem. Commun., 1996, 1257 RSC.
  16. D. Jacoby, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Chem. Soc., Chem. Commun., 1991, 790 RSC.
  17. V. J. Bauer, D. L. J. Clive, D. Dolphin, J. B. Paine, III, F. L. Harris, M. M. King, J. Loder, S.-W. C. Wang and R. B. Woodward, J. Am. Chem. Soc., 1983, 105, 6429 CrossRef CAS.
  18. J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 2810 CrossRef CAS.
  19. M. J. Hynes, J. Chem. Soc., Dalton Trans., 1993, 311 RSC.
  20. W. E. Allen, P. A. Gale, C. T. Brown, V. M. Lynch and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 12 471 CrossRef CAS.
  21. J. L. Sessler, A. Andrievsky, P. A. Gale and V. Lynch, Angew. Chem., Int. Ed. Engl., 1996, 35, 2782 CrossRef CAS.
  22. P. A. Gale, J. L. Sessler, W. E. Allen, N. A. Tvermoes and V. Lynch, Chem. Commun., 1997, 665 RSC.
  23. F. Arnaud-Neu, E. M. Collins, M. Deasy, G. Ferguson, S. J. Harris, B. Kaitner, A. J. Lough, M. A. McKervey, E. Marques, B. L. Ruhl, M. J. Schwing-Weill and E. M. Seward, J. Am. Chem. Soc., 1989, 111, 8681 CrossRef CAS.
  24. P. A. Gale, J. L. Sessler, V. Lynch and P. I. Sansom, Tetrahedron Lett., 1996, 37, 7881 CrossRef CAS.
  25. S. E. J. Bell, J. K. Browne, V. McKee, M. A. McKervey, J. F. Malone, M. O'Leary and A. Walker, unpublished work.
  26. P. A. Gale, J. W. Genge, V. Král, M. A. McKervey, J. L. Sessler and A. Walker, Tetrahedron Lett., in the press Search PubMed.
  27. J. L. Sessler, P. A. Gale and J. W. Genge, unpublished work.
  28. V. Král, P. A. Gale, P. Anzenbacher Jr., K. Jursíková, V. Lynch and J. L. Sessler, Chem. Commun., 1998, 9 RSC.
  29. G. R. Newkome, Y. J. Joo and F. R. Fronczek, J. Chem. Soc. Chem. Commun., 1987, 854 RSC.
  30. D. Jacoby, S. Isoz, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1995, 117, 2793 CrossRef CAS.
  31. C. D. Gutsche and M. Iqbal, Org. Synth., 1990, 68, 234 CAS.
  32. C. D. Gutsche and D. R. Stewart, Org. Prep. Proced. Int., 1993, 25, 137 Search PubMed.
  33. C. D. Gutsche, B. Dhawan, M. Leonis and D. Stewart, Org. Synth., 1990, 68, 238 CAS.
  34. R. L. Jones and C. W. Rees, J. Chem. Soc. (C), 1969, 2249 RSC.
  35. D. S. Black, M. C. Bowyer, N. Kumar and P. S. R. Mitchell, J. Chem. Soc., Chem. Commun., 1993, 819 RSC.
  36. D. S. Black, D. C. Craig and N. Kumar, Tetrahedron Lett., 1995, 36, 8075 CrossRef CAS.