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Homooxacalixarenes: I. Structure, Synthesis, and Chemical Reactions

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Abstract

Data published on the structure, preparation, and chemical reactions of homooxacalixarenes with various number of aromatic fragments and dihomooxabridges in macrocycles were analysed and summarized.

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REFERENCES

  1. Ikeda, A. and Shinkai, S., Chem. Rev., 1997, vol. 97, p. 1713.

    Google Scholar 

  2. Bohmer, V., Angew. Chem. Int. Ed., 1995, vol. 34, p. 713.

    Google Scholar 

  3. Gutsche, C. D., Calixarenes: Monographs in Supramolecular Chemistry, Stoddart, J. F., Ed., Cambridge: The Royal Society of Chemistry, 1989, p. 224.

    Google Scholar 

  4. Gutsche, C.D., Calixarenes: Monographs in Supramolecular Chemistry, Stoddart, J. F., Ed., Cambridge: The Royal Society of Chemistry, 1989, p. 236.

    Google Scholar 

  5. Araki, K., Hashimoto, N., Otsuka, H., and Shinkai, S., J. Org. Chem., 1993, vol. 58, p. 5958.

    Google Scholar 

  6. Araki, K., Inada, K., Otsuka, H., and Shinkai, S., Tetrahedron, 1993, vol. 49, p. 9465.

    Google Scholar 

  7. Yamato, T., Zhang, F., Tsuzuki, H., and Miura, Y., Eur. J. Org. Chem., 2001, p. 1069.

  8. Gutsche, C.D., Dhawan, B., No, K.H., and Muthukrishnan, R., J. Am. Chem. Soc., 1981, vol. 103, p. 3782.

    Google Scholar 

  9. Gutsche, C.D. and Bauer, L., J. Am. Chem. Soc., 1985, vol. 107, p. 6052.

    Google Scholar 

  10. Gutsche, C.D., Muthukrishnan, R., and No, K.H., Tetrahedron Lett., 1979, p. 2213.

  11. Dhawan, B. and Gutsche, C.D., J. Org. Chem., 1983, vol. 48, p. 1536.

    Google Scholar 

  12. Asfari, Z. and Vicens, J., Makromol. Chem., Rapid, Commun., 1989, vol. 10, p. 177.

    Google Scholar 

  13. Sartori, G., Bigi, F., Porta, C., Maggi, R., and Peri, F., Tetrahedron, Lett., 1995, vol. 36, p. 8323.

    Google Scholar 

  14. Yamato, T., Zhang, F., and Yasumatsu, M., J. Chem. Res. (S), 1997, p. 466.

  15. Zerr, P., Mussrabi, M., and Vicens, J., Tetrahedron Lett., 1991, vol. 32, p. 1879.

    Google Scholar 

  16. Miah, M., Romanov, N.N., and Cragg, P.J., J. Org. Chem., 2002, vol. 67, p. 3124.

    Google Scholar 

  17. Ikeda, A., Nobukuni, S., Udzu, Z., and Shinkai, S., Eur. J. Org. Chem., 2000, p. 3287.

  18. Ikeda, A., Suzuki, Y., Yoshimura, M., and Shinkai, S., Tetrahedron, 1998, vol. 54, p. 2497.

    Google Scholar 

  19. Hampton, P.D., Bencze, Z., Tong, W., and Daitch, C.E., J. Org. Chem., 1994, vol. 59, p. 4838.

    Google Scholar 

  20. Atwood, J.L., Barbour, L.J., Nichols, P.J., Raston, C.L., and Sandoval, C.A., Chem. Eur. J., 1999, vol. 5, p. 990.

    Google Scholar 

  21. Masci, B. and Saccheo, S., Tetrahedron, 1993, vol. 49, p. 10739.

    Google Scholar 

  22. Euler, H., Angew. Chem., 1941, vol. 54, p. 458.

    Google Scholar 

  23. No, K.N., Kim, J.S., Shon, O.J., Yang, S.H., Suh, I.H., Kim, J.G., Bartsch, R.A., and Kim, J.Y., J. Org. Chem., 2001, vol. 66, p. 5976.

    Google Scholar 

  24. Hultzsch, K., Kunststoffe, 1962, vol. 52, p. 19.

    Google Scholar 

  25. De Iasi, G. and Masci, B., Tetrahedron Lett., 1993, vol. 34, p. 6635.

    Google Scholar 

  26. Masci, B., Tetrahedron, 2001, vol. 57, p. 2841.

    Google Scholar 

  27. Masci, B., J. Org. Chem., 2001, vol. 66, p. 1497.

    Google Scholar 

  28. Tsubaki, K., Otsubo, T., Tanaka, K., and Fuji, K., J. Org. Chem., 1998, vol. 63, p. 3260.

    Google Scholar 

  29. Tsubaki, K., Mukoyoshi, K., Otsubo, T., and Fuji, K., Chem. Pharm. Bull., 2000, vol. 48, p. 882.

    Google Scholar 

  30. Tsubaki, K., Morimoto, T., Otsubo, T., Kinoshita, T., and Fuji, K., J. Org. Chem., 2001, vol. 66, p. 4083.

    Google Scholar 

  31. Ashram, M., J. Org. Chem., 2001, vol. 66, p. 1473.

    Google Scholar 

  32. Komatsu, N., Tetrahedron, Lett., 2001, vol. 42, p. 1733.

    Google Scholar 

  33. Komatsu, N. and Chishiro, T., J. Chem. Soc., Perkin Trans. I, 2001, p. 1532.

  34. Tarada, T., Rudzinski, J.M., and Shinkai, S., J. Chem. Soc., Perkin, Trans. II., 1992, p. 2109.

  35. Iwamoto, K., Araki, K., and Shinkai, S., J. Org. Chem., 1991, vol. 56, p. 4955.

    Google Scholar 

  36. Iwamoto, K. and Shinkai, S., J. Org. Chem., 1992, vol. 57, p. 7066.

    Google Scholar 

  37. Yamato, T., Haraguchi, M., Nishikawa, J.-I., Ide, S., and Tsuzuki, H., Can. J. Chem., 1998, vol. 76, p. 989.

    Google Scholar 

  38. Ikeda, A., Yoshimura, M., Tani, F., Naruta, Y., and Shinkai, S., Chem. Lett., 1998, p. 587.

  39. Yamato, T., Zhang, F., Sato, T., and Ide, S., J. Chem. Research (S), 2000, p. 10.

  40. Arnaud-Neu, F., Cremin, S., Harris, S., McKervey, M.A., Schwing-Weill, M.-J., Schwinte, P., and Walker, A., J. Chem. Soc., Dalton Trans., 1997, p. 329.

  41. Takeshita, M. and Shinkai, S., Chem. Lett., 1994, p. 125.

  42. Ohkanda, J., Shibui, H., and Katoh, A., Chem. Commun., 1998, p. 375.

  43. Matsumoto, H., Nishio, S., Takeshita, M., and Shinkai, S., Tetrahedron, 1995, vol. 51, p. 4647.

    Google Scholar 

  44. Ikeda, A., Hatano, T., Kawaguchi, M., Suenaga, H., and Shinkai, S., Chem. Commun., 1999, p. 1403.

  45. Yamato, T. and Zhang, F., J. Incl. Phen. Macrocycl. Chem., 2001, vol. 39, p. 55.

    Google Scholar 

  46. Tsubaki, K., Otsubo, T., Kinoshita, T., Kawada, M., Fuji, K., Chem. Pharm. Bull., 2001, vol. 49, p. 507.

    Google Scholar 

  47. Hampton, P.D., Daitch, C.E., Eileen, E.N., New J. Chem., 1996, vol. 20, p. 427.

    Google Scholar 

  48. Dieleman, C.B., Matt, D., Neda, I., Schmutzler, R., Harriman, A., and Yaftian, R., Chem. Commun., 1999, p. 1911.

  49. Takeshita, M., Inokuchi, F., and Shinkai, S., Tetrahedron, Lett., 1995, vol. 36, p. 3341.

    Google Scholar 

  50. Araki, K., Inada, K., and Shinkai, S., Angew. Chem. Int. Ed., 1996, vol. 35, p. 72.

    Google Scholar 

  51. Tsubaki, K., Otsubo, T., Morimoto, T., Maruoka, H., Furukawa, M., Momose, Y., Shang, M., and Fuji, K., J. Org. Chem., 2002, vol. 67, p. 8151.

    Google Scholar 

  52. Tsubaki, K., Morimoto, T., Otsubo, T., and Fuji, K., Org. Lett., 2002, vol. 4, p. 2301.

    Google Scholar 

  53. Araki, K. and Hayashida, H., Tetrahedron Lett., 2000, vol. 41, p. 1807.

    Google Scholar 

  54. Ikeda, A., Udzu, H., Zhong, Z., Shinkai, S., Sakamoto, S., and Yamaguchi, K., J. Am. Chem. Soc., 2001, vol. 123, p. 3872.

    Google Scholar 

  55. Zhong, Z., Ikeda, A., and Shinkai, S., J. Am. Chem. Soc., 1999, vol. 121, p. 11906.

    Google Scholar 

  56. Kawaguchi, M., Ikeda, A., and Shinkai, S., Tetrahedron Lett., 2001, vol. 42, p. 3725.

    Google Scholar 

  57. Marcos, P.M., Ascenso, J.R., Lamartine, R., and Pereira, J.L.C., Tetrahedron, 1997, vol. 53, p. 11791.

    Google Scholar 

  58. Felix, S., Ascenso, J.R., Lamartine, R., and Pereira, J.L.C., Tetrahedron, 1999, vol. 55, p. 8539.

    Google Scholar 

  59. Araki, K., Iwamoto, K., Shinkai, S., and Matsuda, T., Chem. Lett., 1989, p. 1747.

  60. Stewart, D., Krawiec, M., Kashyap, R., Watson, W., and Gutsche, C.D., J. Am. Chem. Soc., 1995, vol. 117, p. 586.

    Google Scholar 

  61. Gutsche, C.D., Dhawan, B., and Levine, J., Tetrahedron, 1983, vol. 39, p. 409.

    Google Scholar 

  62. Groenen, L., van Loon, J.-D., Verboom, W., Harkema, S., Casnati, A., Ungaro, R., Pochini, A., Ugozzoli, F., and Reinhoudt, D., J. Am. Chem. Soc., 1991, vol. 113, p. 2385.

    Google Scholar 

  63. Gutsche, C.D. and Reddy, P., J. Org. Chem., 1991, vol. 56, p. 4783.

    Google Scholar 

  64. Grotenhuis, P., Kollman, P., Groenen, L., Reinhoudt, D., van, Hummel, G., Ugozzoli, F., and Andreetti, G., J. Am. Chem. Soc., 1990, vol. 112, p. 4165.

    Google Scholar 

  65. Arnaud-Neu, F., Collins, E. M., Deasy, M., Ferguson, G., Harris, S.J., Kaitner, B., Lough, A.J., McKervey, M.A., Marques, E., Ruhl, B.L., Schwing-Weill, M., and Seward, E.M., J. Am. Chem. Soc., 1989, vol. 111, p. 8681.

    Google Scholar 

  66. Ferguson, G., Kaitner, B., McKervey, M.A., and Seward, E.M., Chem. Commun., 1987, p. 584.

  67. Arduini, A., Ghidini, E., Pochini, A., Ungaro, R., Andreeti, G.D., Calestani, G., and Ugozzoli, F., J. Incl. Phen., 1988, vol. 6, p. 119.

    Google Scholar 

  68. Marcos, P.M., Ascenso, J.R., Lamartine, R., and Pereira, J.L.C., J. Org. Chem., 1998, vol. 63, p. 69.

    Google Scholar 

  69. Marcos, P.M., Ascenso, J.R., Segurado, M.A.P., and Pereira, J.L.C., Tetrahedron, 2001, vol. 57, p. 6977.

    Google Scholar 

  70. Marcos, P.M., Ascendo, J.R., and Pereira, J.L.C., Eur. J. Org. Chem., 2002, p. 3034.

  71. Felix, S., Ascenso, J.R., Lamartine, R., and Pereira, J.L.C., Synth. Commun., 1998, vol. 28, p. 1793.

    Google Scholar 

  72. Marcos, P.M., Felix, S., Ascenso, J.R., Santos, M.A., Segurado, M.A.P., and Pereira, J.L.C., Tetrahedron, 2002, vol. 58, p. 9223.

    Google Scholar 

  73. Arnaud-Neu, F., Cremin, S., Cunningham, D., Harris, S.J., Mc-Ardle, P., McKervey, M.A., McManus, M., Schwing-Weil, M.J., and Ziat, K., J. Incl. Phen. Mol. Recogn. Chem., 1991, vol. 10, p. 329.

    Google Scholar 

  74. Arnaud-Neu, F., Barrett, G., Harris, S.J., Owens, M., McKervey, M.A., Schwing-Weill, M.-J., and Schwinte, P., Inorg. Chem., 1993, vol. 32, p. 2644.

    Google Scholar 

  75. No, K., Lee, J.H., Yang, S.H., Yu, S.H., Cho, M.H., Kim, M.J., and Kim, J.S., J. Org. Chem., 2002, vol. 67, p. 3165.

    Google Scholar 

  76. No, K., Lee, J.H., Yang, S.H., Noh, K.H., Lee, S.W., and Kim, J.S., Tetrahedron, 2003, vol. 59, p. 2403.

    Google Scholar 

  77. Oueslati, I., Abidi, R., Asfari, Z., Vicens, J., Masci, B., Thuery, P., and Nierlich, M., J. Incl. Phen. Macrocycl. Chem., 2001, vol. 39, 353.

    Google Scholar 

  78. Calixarenes 2001, Asfari, Z., Buhmer, V., Harrowfield, J., and Vicens, Eds., J. Kluwer Academic: Dordrecht, The Netherlands, 2001.

    Google Scholar 

  79. Takeshita, M. and Shinkai, S., Bull. Chem. Soc. Jpn., 1995, p. 1088.

  80. Shokova, E.A. and Kovalev, V.V., Zh. Org. Khim., 2003, vol. 39, p. 13.

    Google Scholar 

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Shokova, E.A., Kovalev, V.V. Homooxacalixarenes: I. Structure, Synthesis, and Chemical Reactions. Russian Journal of Organic Chemistry 40, 607–643 (2004). https://doi.org/10.1023/B:RUJO.0000043707.97314.52

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