Skip to main content
Log in

Abstract

A new type of host is introduced:all-homocalixarenes. Phane syntheses leading to molecules which may be termed, in the most general sense, homocalixarenes, are outlined in a brief overview. The design, synthesis, conformations and host properties ofall-homocalixarenes andall-homocalixpyridines are described in detail.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. C. D. Gutsche:Calixarenes, Monographs in Supramolecular Chemistry, Vol. 1, Ed. J. F. Stoddard, The Royal Society of Chemistry, Cambridge (1989).

    Google Scholar 

  2. J. Vicens and V. Böhmer (Eds.):Calixarenes: A Versatile Class of Macrocyclic Compounds, Kluwer Academic Publishers, Dordrecht (1991).

    Google Scholar 

  3. C. D. Gutsche:Acc. Chem. Res. 16, 161 (1983).

    Google Scholar 

  4. F. Vögtle:Cyclophane Chemistry, Wiley, Chichester (1993).

    Google Scholar 

  5. J. L. Sessler and A. K. Burrell:Top Curr. Chem. 161, 177 (1991).

    Google Scholar 

  6. M. M. Pellegrin:Recl. Trav. Chim. Pays-Bas 18, 457 (1989).

    Google Scholar 

  7. K. Burri and W. Jenny:Helv. Chim. Acta 50, 1978 (1967).

    Google Scholar 

  8. E. Müller and G. Röscheisen:Chem. Ber. 90, 543 (1957).

    Google Scholar 

  9. K. Burri and W. Jenny:Chimia 20, 403 (1966).

    Google Scholar 

  10. W. Jenny and K. Burri:Chimia 20, 436 (1966).

    Google Scholar 

  11. W. Jenny and K. Burri:Chimia 21, 186 (1967).

    Google Scholar 

  12. W. Jenny and K. Burri:Chimia 21, 472 (1967).

    Google Scholar 

  13. W. Jenny and R. Paioni:Chimia 22, 142 (1968).

    Google Scholar 

  14. R. Paioni and W. Jenny:Helv. Chim. Acta 52, 2041 (1969).

    Google Scholar 

  15. M. Tashiro and T. Yamato:J. Org. Chem. 46, 1543 (1981).

    Google Scholar 

  16. S. Takahashi and N. Mori:J. Chem. Soc., Perkin Trans., 1 2029 (1991).

    Google Scholar 

  17. F. Vögtle:Liebigs Ann. Chem. 728, 17 (1969).

    Google Scholar 

  18. K. Böckmann and F. Vögtle:Chem. Ber. 114, 1048 (1981).

    Google Scholar 

  19. M. Tashiro and T. Yamato:J. Org. Chem. 46. 1543 (1981).

    Google Scholar 

  20. M. Tashiro, T. Watanabe, A. Tsuge, T. Sawada, and S. Mataka:J. Org. Chem. 54, 2632 (1989).

    Google Scholar 

  21. A. Tsuge, T. Sawada, S. Mataka, N. Nishiyama, H. Sakashita, and M. Tashiro:J. Chem. Soc., Chem. Commun. 1066 (1990).

  22. M. Tashiro, A. Tsuge, T. Sawada, T. Makishima, S. Horie, T. Arimura, and S. Mataka, T. Yamato:J. Org. Chem. 55, 2404 (1990).

    Google Scholar 

  23. A. Tsuge, T. Sawada, S. Mataka, N. Nishiyama, H. Sakashita, and M. Tashiro:J. Chem. Soc., Perkin Trans. 1 1489 (1992).

    Google Scholar 

  24. T. Yamato, Y. Saruwatari, S. Nagayama, K. Maeda, and M. Tashiro:J. Chem. Soc., Chem. Commun. 861 (1992).

  25. T. Yamato, Y. Saruwatari, S. Nagayama, K. Maeda, and M. Tashiro:J. Chem. Soc., Chem. Commun. 861 (1992).

  26. T. Yamato, Y. Saruwatari, L. K. Doamekpor, K.-i. Hasegawa, and M. Koike:Chem. Ber. 126, 2501 (1993).

    Google Scholar 

  27. F. Vögtle and M. Zuber:Synthesis 543 (1972).

  28. T. Sato, M. Wakabayashi, and K. Hata:Bull. Chem. Soc. Jpn. 43, 3632 (1970).

    Google Scholar 

  29. R. B. Bates, S. Gangwar, V. V. Kane, K. Suvannachut, and S. R. Taylor:J. Org. Chem. 56, 1696 (1991).

    Google Scholar 

  30. D. H. Burns, J. D. Miller, and J. Santana:J. Org. Chem. 58, 6526 (1993).

    Google Scholar 

  31. C. D. Gutsche, B. Dhawan, K. H. No, and R. Muzhukrishnan:J. Am. Chem. Soc. 103, 3782 (1981).

    Google Scholar 

  32. K. Hultzsch:Kunstoffe 52, 19 (1962).

    Google Scholar 

  33. B. Dhawan and C. D. Gutsche:J. Org. Chem. 48, 1536 (1983).

    Google Scholar 

  34. T. Tanno and Y. Mukoyama:Netsu. Kokasei Jushi 2, 132 (1981);Chem. Abstr. 96, 52791k (1982).

    Google Scholar 

  35. Y. Mukoyama and T. Tanno:Org. Coat. Plast. Chem. 40, 894 (1979).

    Google Scholar 

  36. H. Takemura, K. Yoshimura, I. U. Khan, T. Shinmyozu, and T. Inazu:Tetrahedron Lett. 33, 5775 (1992).

    Google Scholar 

  37. S. Mizogami, N. Osaka, T. Otsubo, Y. Sakata, and S. Misumi:Tetrahedron Lett. 799 (1974).

  38. M. Chastrette and F. Chastrette:J. Chem. Soc., Chem. Commun. 534 (1973).

  39. A. G. S. Högberg and M. Weber:Acta Chem. Scand. Ser. B 37, 55 (1983).

    Google Scholar 

  40. R. M. Musau and A. Whiting:J. Chem. Soc., Chem. Commun. 1029 (1993).

  41. M. Ahmed and O. Meth-Cohn:Tetrahedron Lett. 1493 (1969).

  42. M. Ahmed and O. Meth-Cohn:J. Chem. Soc. C 2104 (1971).

  43. T. Thiemann, Y. Lee, Y. Nagano, M. Tashiro:Book of Abstr. ‘Second Workshop on Calixarenes and Related Compounds’ in Krume, Fukuoka, Japan,PS/A28 (1993).

  44. E. Vogel, P. Röhrig, M. Sicken, B. Knipp, A. Herrmann, M. Pohl, and H. Schmickler, J. Lex:Angew. Chem. 101, 1683 (1989);Angew. Chem. Int. Ed. Engl. 28, 1651 (1989).

    Google Scholar 

  45. P. Rothemund and C. L. Gage:J. Am. Chem. Soc. 77, 3340 (1955).

    Google Scholar 

  46. J. S. Lindsay, I. C. Schreiman, H. C. Hsu, P. C. Kearney, and A. M. Marguerettaz:J. Org. Chem. 52, 827 (1987).

    Google Scholar 

  47. G. R. Newkome, Y. J. Joo, K. J. Theriot, and F. R. Fronczek:J. Am. Chem. Soc. 108 6074–6075 (1986).

    Google Scholar 

  48. G. R. Newkome, Y. J. Joo, and F. R. Fronczek:J. Chem. Soc., Chem. Commun. 854 (1987).

  49. W. Jenny and H. Holzrichter:Chimia 21, 509 (1967).

    Google Scholar 

  50. W. Jenny and H. Holzrichter:Chimia 22, 139 (1968).

    Google Scholar 

  51. W. Jenny and H. Holzrichter:Chimia 22, 306 (1968).

    Google Scholar 

  52. W. Jenny and H. Holzrichter:Chimia 23, 158 (1968).

    Google Scholar 

  53. Th. Kauffmann, G. Beisser, W. Sahm, and A. Woltermann:Angew. Chem. 82, 815 (1970);Angew. Chem. Int. Ed. Engl. 9, 808 (1970).

    Google Scholar 

  54. Cf.: G. Brodesser, R. Güther, R. Hoss, S. Meier, S. Ottens-Hildebrandt, J. Schmitz, and F. Vögtle:Pure Appl. Chem. 65, 2325 (1993); G. Brodesser, J. Schmitz, F. Vögtle, K. Gloe, O. Heitzsch, and H. Stephan:Book of Abstr. ‘Second Workshop on Calixarenes and Related Compounds’ in Kurume, Fukuoka, Japan,IL-8 (1993); G. Brodesser, R. Güther, S. Meier, S. Ottens-Hildebrandt, J. Schmitz, and F. Vögtle:Book of Abstr.: ‘XVIII. Int. Symposium on Macrocyclic Chemistry’ in Enschede, the Netherlands,P-12 (1993); F. Vögtle:Ann. Quim. 89, 29 (1993).

    Google Scholar 

  55. F. Vögtle, J. Schmitz, and M. Nieger:Chem. Ber. 125, 2523 (1992).

    Google Scholar 

  56. J. Schmitz, F. Vögtle, M. Nieger, K. Gloe, H. Stephan, O. Heitzsch, H.-J. Buschmann, W. Hasse, and K. Cammann:Chem. Ber. 126, 2483 (1993).

    Google Scholar 

  57. J. Schmitz, F. Vögtle, M. Nieger, K. Gloe, H. Stephan, O. Heitzsch, H.-J. Buschmann:Supramol. Chem. 3 (1994), in press.

  58. F. Vögtle, G. Brodesser, M. Nieger, K. Rissanen:Recl. Trav. Chim. Pays-Bas 112, 325 (1993).

    Google Scholar 

  59. A. Ninagawa and H. Matsuda:Makromol. Chem., Rapid Commun. 3, 65 (1982).

    Google Scholar 

  60. M. A. Markowitz, V. Janout, D. G. Gastner, and S. L. Regen:J. Am. Chem. Soc. 111, 8192 (1989).

    Google Scholar 

  61. D. R. Stewart, C. D. Gutsche:Org. Prep. Proced. Int. 25, 137 (1993).

    Google Scholar 

  62. T. Sato, M. Wakabayshi, K. Hata, and M. Kainosho:Tetrahedron 27, 2737 (1971).

    Google Scholar 

  63. K. Araki, N. Hashimoto, H. Otsuka, and S. Shinkai:J. Org. Chem. 56, 5958 (1993).

    Google Scholar 

  64. K. Araki, K. Inada, H. Otsuka, and S. Shinkai:Tetrahedron 49, 9465 (1990).

    Google Scholar 

  65. A. Tsuge, S. Sonoda, S. Mataka, and M. Tashiro:Chem. Lett. 1173 (1990).

  66. H.-B. Mekelburger, J. Gross, J. Schmitz, M. Nieger, and F. Vögtle:Chem. Ber. 126, 1713 (1993).

    Google Scholar 

  67. Cooperation with Prof. Dr. K. Gloe, Dresden.

  68. K. Gloe, H. Stephan, O. Heitzsch, J. Schmitz, and F. Vögtle:Book of Abstr.: ‘XVIII. Int. Symposium on Macrocyclic Chemistry’ in Enschede, the Netherlands,A-70 (1993).

  69. H. Stephan, K. Gloe, O. Heitzsch, G. Brodesser, and F. Vögtle:Book of Abstr.: ‘24. GDCH-Hauptversammlung’, in Hamburg, Germany,SUP 9 (1993).

  70. Cooperation with Prof. Dr. K. Cammann, Münster.

  71. J. Reinbold, B. Ahlers, W. Hasse, K. Cammann, G. Brodesser, and F. Vögtle:Book of Abstr.: ‘XVIII. Int. Symposium on Macrocyclic Chemistry’ in Enschede, the Netherlands,B-55, 56 (1993).

  72. W. Hasse, K. Cammann, F. Vögtle, and G. Brodesser:Book of Abstr.: ‘Eurosensor VII’, in Budapest, Hungary,AP-24, 4430-1 (1993).

  73. Cf.: R. M. Izatt, J. D. Lamb, R. T. Hawkins, P. R. Brown, S. R. Izatt, and J. J. Christensen:J. Am. Chem. Soc. 105 1782 (1983); S. R. Izatt, R. T. Hawkins, J. J. Christensen, and R. M. Izatt:J. Am. Chem. Soc. 107, 63 (1985).

    Google Scholar 

  74. Cooperation with Dr. H.-J. Buschmann, Krefeld.

  75. R. Perrin and S. Harris: inCalixarenes: A Versatile Class of macrocyclic compounds, J. Vicens and V. Böhmer (Eds.), Kluwer Academic Publishers, Dordrecht, p. 241 (1991).

    Google Scholar 

  76. Cf.: S. Shinkai, T. Otsuka, K. Araki, and T. Matsuda:Bull. Chem. Soc. Jpn. 62, 4055 (1989).

    Google Scholar 

  77. Cooperation with Prof. Dr. M. Przybylski, Konstanz.

  78. F. M. Menger, S. Broccini, and X. Chen:Angew. Chem. 104, 1542 (1992);Angew. Chem. Int. Ed. Engl. 31, 1492 (1992).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

This paper is dedicated to the commemorative issue on the 50th anniversary of calixarenes.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Brodesser, G., Vögtle, F. Homocalixarenes and homocalixpyridines. J Incl Phenom Macrocycl Chem 19, 111–135 (1994). https://doi.org/10.1007/BF00708978

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00708978

Key words

Navigation