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O-Ethoxycarbonylmethoxy esters of homocalix[n]naphthalenes: synthesis and recognition behaviour towards alkali cations

  • Huu-Anh Tran
  • Muhammad Ashram
  • Shehadeh Mizyed
  • David W. Thompson
  • Paris E. Georghiou
Original Article

Abstract

The condensation of 1,2-bis(3-hydroxy-2-naphthyl)ethane and formaldehyde under basic conditions was successfully employed for the synthesis of two new large-ring n-homocalixnaphthalenes 5 and 6. The synthetic yields using a relatively larger reaction scale were higher than those obtained by the sulphur extrusion approach. O-Alkylation of these homocalixnaphthalenes afforded the corresponding hexa- and octa-O-ester derivatives 5a and 6a respectively. The new naphthalene-ring based macrocycle 5a demonstrated high extraction capability for K+ under the conditions studied.

Graphical abstract

O -Ethoxycarbonylmethoxy esters of homocalix[ n ]naphthalenes: synthesis and recognition behaviour towards alkali cations

Huu-Anh Tran, Muhammad Ashram, Shehadeh Mizyed, David W. Thompson and Paris E. Georghiou*

The condensation of 1,2-bis(3-hydroxy-2-naphthyl)ethane and formaldehyde under basic conditions was successfully employed for the synthesis of two new large-ring n-homocalixnaphthalenes 5 and 6.

Keywords

Calixarenes Homocalixarenes Calixnaphthalenes Homocalixnaphthalenes Alkali metal complexation 

Notes

Acknowledgement

This research was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC) and the Department of Chemistry, Memorial University of Newfoundland.

References

  1. 1.
    (a) Gutsche, C.D.: In: Stoddart, J.F., (ed.) Calixarenes, Monographs in Supramolecular Chemistry, pp. 59–60. The Royal Society of Chemistry, (1989) and references cited therein; (b) Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J. (eds.): Calixarenes 2001. Kluwer Acadamic Publishers, Dordrecht, The Netherlands (2001)Google Scholar
  2. 2.
    (a) Brodesser, G., Vögtle, F.: Homocalixarenes and homocalixpyridines. J. Incl. Phenom. Mol. Recognit. Chem. 19, 111–135 (1994); (b) Schmitz, J., Vögtle, F., Nieger, M., Gloe, K., Stephen, H., Heitzsch, O., Buschmann, H.-J., Hasse, W., Cammann, K.: All-Homocalixarenes: carbocyclic hosts with intra- and extraannular ligand arms. Chem. Ber. 126, 2483–2491 (1993)Google Scholar
  3. 3.
    Ibach, S., Prautzsch, V., Vötgle, F.: Acc. Chem. Res. 32, 729–740 (1999)CrossRefGoogle Scholar
  4. 4.
    Nakamura, Y., Fuji, T., Inokuma, S., Nishimura, J.: Homocalixarenes. In: Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J. (eds.) Calixarenes 2001, pp. 219–234. Kluwer Acadamic Publishers, Dordrecht, The Netherlands (2001) and references cited thereinGoogle Scholar
  5. 5.
    (a) Yamato, T., Saruwatari, Y., Nagayama, S., Maeda, K., Tashiro, M.: Preparation and conformational properties of tetrahydroxy [3.1.3.1] metacyclophanes. J. Chem. Soc. Chem. Commun. 861–862 (1992); (b) Yamato, T., Saruwatari, Y., Yasumatsu, M.: Synthesis and conformational studies of tetrahydroxy [3.1.3.1] metacyclophanes and electrophilic aromatic substitution of their tetramethoxy derivatives. J. Chem. Soc. Perkin Trans. 1, 1725–1730 (1997); (c) Yamato, T., Saruwatari, Y., Yasumatsu, M.: Synthesis and conformational studies of regio- and conformational isomers derived by O-alkylation of tetrahydroxy [3.1.3.1] metacyclophane. J. Chem. Soc. Perkin Trans. 1, 1731–1737 (1997)Google Scholar
  6. 6.
    (a) Thuéry, P., Jeong, T.G., Yamato, T.: Crystal Structures of Uranyl Ion Complexes of Tetrahydroxy [3.1.3.1] metacyclophane (Homocalix[4]arene). Supramol. Chem. 15, 359–365 (2003); (b) Salmon, L., Thuéry, P., Miyamoto, S., Yamato, T., Ephritikhine, M.: Uranium(V) and uranium(IV/V) mixed valence complexes with p-tert-butylhomocalix[n]arenes (n = 4, 6). Polyhedron 62, 1250–1251 (2006)Google Scholar
  7. 7.
    Yamato, T., Kohno, K., Tsuchihashi, K.: Synthesis, structures and ion selectivity of homocalix[3]arene thioketals derived from homocalix[3]arene ketones. J. Incl. Phenom. Macro. Chem. 43, 137–144 (2002)CrossRefGoogle Scholar
  8. 8.
    Yamato, T.: Synthesis, conformations and inclusion properties of homocalix[3]arenes. J. Incl. Phenom. Mol. Recognit. Chem. 32, 195–207 (1998)CrossRefGoogle Scholar
  9. 9.
    Yamato, T., Iwasa, T., Zhang, F.: Synthesis and ion selectivity of tetrakis[(N,N-dialkylaminocarbonyl) methoxy]homocalix[4]arenes. J. Incl. Phenom. Macro. Chem. 39, 285–294 (2001)CrossRefGoogle Scholar
  10. 10.
    Yamato, T., Saruwatari, Y., Yasumatsu, M., Tsuzuki, H.: Synthesis and ion selectivity of conformers of tetraalkyl esters derived from 9,16,25,32-tetrahydroxy[3.1.3.1]metacyclophane. New J. Chem. 1351–1358 (1998)Google Scholar
  11. 11.
    Georghiou, P.E., Miller D.O., Tran, A.H., Al-Saraierh, H., Li, Z., Ashram, M., Chowdhury, S., Mizyed, S.: Calixnaphthalenes: deep, electron-rich naphthalene ring-containing calixarenes. The first decade. Synlett 6, 879–891 (2005)CrossRefGoogle Scholar
  12. 12.
    Georghiou, P.E., Li, Z., Ashram, M., Miller, D.O.: Syntheses of dihomocalix[4]naphthalenes: first members of a new class of [1.2.1.2](1,3)naphthaleneophanes. J. Org. Chem. 61, 3865–3869 (1996)CrossRefGoogle Scholar
  13. 13.
    (a) Gutsche, C.D., Dhawan, B., No, K.H., Muthukrishnan, R.: Calixarenes. 4. The synthesis, characterization, and properties of the calixarenes from p-tert-butylphenol. J. Am. Chem. Soc. 103, 3782–3792 (1981); (b) Izatt, R.M., Lamb, J.D., Hawkins, R.T., Brown, P.R., Izatt, S.R., Christensen, J.J.: Selective M+–H+ coupled transport of cations through a liquid membrane by macrocyclic calixarene ligands. J. Am. Chem. Soc. 105, 1782–1785 (1983); (c) Mckervey, M.C., Seward, E.M., Ferguson, G., Ruhl, B., Harris, S.J.: Synthesis, X-ray crystal structures, and cation transfer properties of alkyl calixaryl acetates, a new series of molecular receptors. J. Chem. Soc. Chem. Commun. 388–390 (1985); (d) Ishikawa, Y., Kunitake, T., Matsuda, T., Otsuka, T., Shinkai, S.: Formation of calixarene monolayers which selectively respond to metal ions. J. Chem. Soc. Chem. Commun. 736–738 (1989); (e) Davis, F., Otoobe, L., Short, R., Stirling, C.J.M.: Selective Ion Binding by Langmuir-Blodgett Films of Calix(8)arenes. Langmuir 12, 1892–1894 (1996) (f) Dei, L., Casnati, A., Lonostro, P., Baglioni, P.: Selective Complexation by p-tert-Butylcalix[6]arene in Monolayers at the Water-Air Interface. Langmuir 11, 1268–1272 (1995); (g) Ludwig, R., Matsumoto, H., Takeshita, M., Ueda, K., Shinkai, S.: Study on monolayers of metal complexes of calixarenes and their luminescence properties. Supramol. Chem. 4, 319–327 (1995); (h) Iwamoto, K., Shinkai, S.: Synthesis and ion selectivity of all conformational isomers of tetrakis[(ethoxycarbonyl)methoxy]calix[4]arene. J. Org. Chem. 57, 7066–7073 (1992)Google Scholar
  14. 14.
    Ashram, M., Mizyed, S., Georghiou, P.E.: Ester derivatives of hexahomotrioxacalix[3]naphthalenes: conformational and binding properties with alkali metal cations. Org. Biomol. Chem. 1, 599–603 (2003)CrossRefGoogle Scholar
  15. 15.
    Georghiou, P.E., Tran, A.H., Mizyed, S., Bancu, M., Scott, L.T.: Concave polyarenes with sulfide-linked flaps and tentacles: new electron-rich hosts for fullerenes. J. Org. Chem. 70, 6158–6163 (2005)CrossRefGoogle Scholar
  16. 16.
    Ma, J.C., Dougherty, D.A.: The cation-interaction. Chem. Rev. 97, 1303–1324 (1997)CrossRefGoogle Scholar
  17. 17.
    Ferdani, R., Barbour, L.J., Gokel, G.W.: Cation-π interactions in the crystal structures of alkali metal calixarene complexes. J. Supramol. Chem. 2, 343–348 (2002)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2007

Authors and Affiliations

  • Huu-Anh Tran
    • 1
  • Muhammad Ashram
    • 2
  • Shehadeh Mizyed
    • 3
  • David W. Thompson
    • 1
  • Paris E. Georghiou
    • 1
  1. 1.Department of ChemistryMemorial University of NewfoundlandSt. John’sCanada
  2. 2.Department of ChemistryMu’Tah UniversityAl KarakJordan
  3. 3.Department of ChemistryYarmouk UniversityIrbidJordan

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