Abstract
Rigidified calix[4]arene analogs were synthesized fromsyn-[2.n]metacyclophanes as a building block. Their structure was firmly locked in the cone conformation. An enlarged calix[4]arene analog was obtained after the cyclobutane ring cleavage of the parent analog by Birch reduction. Several ionophores have been derived from the analogs and been found to select the larger ions during the extraction of alkali metals, transition metals, and lanthanoids. The ionophore having oligoethylene glycol units showed an effective catalytic activity for SN2 reactions such as ester synthesis, Williamson ether synthesis, and Finkelstein reaction in several media.
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C.D. Gutsche:Acc. Chem. Res. 16, 161 (1983); S. Shinkai:J. Incl. Phenom. 7, 193 (1989).
D.W. Chasar:J. Org. Chem. 50, 545 (1985); V. Böhmer, H. Goldmann, and W. Vogt:J. Chem. Soc., Chem. Commun. 1985, 667.
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. 111, 8681 (1989); V. Böhmer, W. Vogt, and H. Goldmann:J. Org. Chem. 55, 2569 (1990); E. Ghidini, F. Ugozzoli, R. Ungaro, S. Harkema, A.A. El-Fadl, and D.N. Reinhoudt:J. Am. Chem. Soc. 112, 6979 (1990).
Y. Okada, K. Sugiyama, Y. Wada, and J. Nishimura:Tetrahedron Lett. 31, 107 (1990); Y. Okada, K. Sugiyama, M. Kurahayashi, and J. Nishimura:ibid. 32, 2367 (1991); Y. Okada, S. Mabuchi, M. Kurahayashi, and J. Nishimura:Chem. Lett. 1991, 1345.
Y. Okada, F. Ishii, Y. Kasai, and J. Nishimura:Chem. Lett. 1992, 755; Y. Okada, F. Ishii, Y. Kasai, and J. Nishimura:Tetrahedron Lett. 34, 1971 (1993); Y. Okada, Y. Kasai, F. Ishii, and J. Nishimura:J. Chem. Soc., Chem. Commun. 1993, 976.
D.J. Cram:Science 219, 1177 (1983);Synthesis of Macrocycles, ed. by R.M. Izatt and J.J. Christensen, Wiley, New York, 1987; C.D. Gutsche:Calixarenes, Royal Society of Chemistry, London, 1989; K. Koga and K. Odashima:J. Incl. Phenom. 7, 53 (1989).
J. Nishimura, N. Yamada, Y. Horiuchi, E. Ueda, A. Ohbayashi, and A. Oku:Bull. Chem. Soc. Jpn. 59, 2035 (1986).
Organic Reactions Vol. V, ed. by R. Adams, Wiley, New York, 1949, Chap. 5.
J. Nishimura, H. Doi, E. Ueda, A. Ohbayashi, and A. Oku:J. Am. Chem. Soc. 109, 5293 (1987).
M. Yamamoto, T. Asanuma, and Y. Nishijima:J. Chem. Soc., Chem. Commun. 1975, 53; T. Asanuma, M. Yamamoto, and Y. Nishijima:ibid. 1975, 56.
H. Nozaki, I. Otani, R. Noyori, and M. Kawanisi:Tetrahedron 24, 2183 (1968).
J. Nishimura, A. Ohbayashi, H. Doi, K. Nishimura, and A. Oku:Chem. Ber.:121, 2019 (1988).
T. Kamada and O. Yamamoto:Bull. Chem. Soc. Jpn. 52, 1159 (1979).
T. Kamada and O. Yamamoto:Bull. Chem. Soc. Jpn. 53, 994 (1980).
D. Krois and H. Lehner:Tetrahedron 38, 3319 (1982).
R.H. Mitchell, T.K. Vinod, and G.W. Bushnell:J. Am. Chem. Soc. 107, 3340 (1985); R.H. Mitchell, G.J. Bodwell, T.K. Vinod, and K.S. Weerawarna:Tetrahedron Lett. 29, 3287 (1988).
Y.-H. Lai and S.-M. Lee:J. Org. Chem. 53, 4472 (1988).
H. Meier, E. Praß, and K. Noller:Chem. Ber. 121, 1637 (1988).
T.W. Greene:Protective Groups in Organic Synthesis, Wiley, New York, 1981, p. 91.
Y. Okada, Y. Kasai, and J. Nishimura:Synlett. in press.
A. Greenberg and J.F. Liebman:Strained Organic Molecules, Academic Press, New York (1978), p. 58; J. Nishimura, A. Ohbayashi, E. Ueda, and A. Oku:Chem. Ber.:121, 2025 (1988); B.P. Mundy and M.G. Ellerd:Named Reactions and Reagents in Organic Synthesis, Wiley, New York, 1988, p. 31.
A. Arduini, A. Pochini, S. Reverberi, and R. Ungaro:Tetrahedron 42, 2089 (1986).
S.-K. Chang and I. Cho:Chem. Lett. 1984, 477; M.A. McKervey, E.M. Seward, G. Ferguson, B. Ruhl, and S.J. Harris:J. Chem. Soc., Chem. Commun. 1985, 388; T. Nagasaki and S. Shinkai:Bull. Chem. Soc. Jpn. 65, 471 (1992).
H. Taniguchi and E. Nomura:Chem. Lett. 1988, 1773.
Y. Okada, Y. Sugitani, Y. Kasai, and J. Nishimura:Bull. Chem. Soc. Jpn. 67, 586 (1994).
D. Landini and F. Montanari:J. Chem. Soc., Chem. Commun. 1974, 879; M. Cinquini and F. Montanari:ibid. 1975, 393.
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This paper is dedicated to the commemorative issue on the 50th anniversary of calixarenes.
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Okada, Y., Nishimura, J. The design of cone-fixed calix[4]arene analogs by takingsyn-[2.n]metacyclophanes as a building block. J Incl Phenom Macrocycl Chem 19, 41–53 (1994). https://doi.org/10.1007/BF00708973
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DOI: https://doi.org/10.1007/BF00708973