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1,3-Alternate and C-1,2-Alternate Tetrahomodioxacalix[4]crowns. Crystal Structures and Metal Ion Complexation

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Abstract

Two novel tetrahomodioxacalix[4]crowns with crown-5 and crown-6 rings weresynthesized. From X-ray crystal structures, homooxacalix[4]crown-5 (3) andhomooxacalix[4]crown-6 (2) were found to be in the 1,3-alternate and theC-1,2-alternate conformations, respectively. Homooxacalix[4]crown-5 (1)shows a marked selectivity for cesium ion over other metal ions tested.

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References

  1. C.D. Gutsche: Calixarenes, Royal Society of Chemistry, Cambridge (1989). (b) C.D. Gutsche: In R.M. Izatt and J.J. Christensen (eds.), Synthesis of Macrocycles: Design of Selective Complexing Agents,Wiley, New York (1987) pp. 93. (c) C.D. Gutsche: Calixarenes Revisited, Royal Society of Chemistry, Cambridge (1998). (d) V. Böhmer and M.A. McKervey: Chemie in unserer Zeit. 195 (1991). (e) C.D. Gutsche: In J.F. Stoddart (ed.), Calixarenes, Monographs in Supramolecular Chemistry, Royal Society of Chemistry, Cambridge, U.K. (1989), Vol. 1. (f) C.D. Gutsche: In J.L. Atwood, J.E.D. Davies and D.D. MacNicol (eds.), Inclusion Compounds, Oxford University Press, New York, Vol. 4 (1991), pp. 27-63. (g) J.-D. Van Loon, W. Verboom, and D.N. Reinhoudt: Org. Prep. Proc. Int. 24, 437-462 (1992).

    Google Scholar 

  2. A. Casnati, R. Ungaro, Z. Asfari, and J. Vicens: In Z. Asfari, V. Böhmer, J. Harrowfield, and J. Vicens (eds.), Calixarenes 2001, Kluwer Academic Publishers, Dordrecht, Holland, 2001.

    Google Scholar 

  3. J.G. Kim, I.H. Suh, J.Y. Yoon, and J.H. Lee: J. Org. Chem. 65, 7215 (2000). (b) V. Böhmer: Angew. Chem., Int. Ed. Engl. 34, 713 (1995).

    Google Scholar 

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

    Google Scholar 

  5. C. Bavoux, F. Vocanson, M. Perrin, and R. Lamartine: J. Incl. Phenom. Mol. Recogn. Chem. 22, 119 (1995).

    Google Scholar 

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

    Google Scholar 

  7. P. Thuéry, M. Nierlich, J. Vicens, and B. Masci: Acta Cryst. C57, 70 (2001). (b) Z. Asfari, J.M. Harrowfield, M.I. Ogden, J. Vicens and A.H. White: Angew. Chem., Int. Ed. Engl. 30, 854 (1991).

    Google Scholar 

  8. J.M. Harrowfield, M.I. Ogden, and A.H. White: J. Chem. Soc., Dalton Trans. 979 (1991).

  9. P.M. Marcos, J.R. Ascenso, R. Lamartine, and J.L.C. Pereira: Tetrahedron 53, 11791 (1997).

    Google Scholar 

  10. S. Felix, J.R. Ascenso, R. Lamartine, and J.L.C. Pereira: Syn. Commun. 28, 1793 (1998).

    Google Scholar 

  11. K. No, J.H. Lee, S.H. Yang, M.J. Kim, and J.S. Kim: J. Org. Chem. 67, 3165 (2002).

    Google Scholar 

  12. B. Masci and S. Saccheo: Tetrahedron Lett. 49, 10739 (1993). (b) B. Masci, M. Gabrielli, S.L. Mortera, M. Nierlich, and P. Thuéry: Polyhedron 21, 1125 (2002).

    Google Scholar 

  13. K. No, J.S. Kim, O.J. Shon, S.H. Yang, I.H. Suh, J.G. Kim, R.A. Bartsch, and J.Y. Kim: J. Org. Chem. 66, 5976 (2001).

    Google Scholar 

  14. A. Casnati, A. Pochini, R. Ungaro, F. Ugozzoli, F. Arnaud-Neu, S. Fanni, M.-J. Schwing, R.J.M. Egberink, F. de Jong, and D.N. Reinhoudt: J. Am. Chem. Soc. 117, 2767 (1995).

    Google Scholar 

  15. P. Thuéry, M. Nierlich, V. Lamare, J.-F. Dozol, Z. Asfari, and J. Vicens: J. Incl. Phen. Macro. Chem. 36, 375 (2000). (b) J.S. Kim, I.H. Suh, J.K. Kim, and M.H. Cho: J. Chem. Soc., Perkin Trans. 1 2307 (1998). (c) J.S. Kim, A. Ohki, R. Ueki, T. Ishizuka, T. Shimotashiro, and S. Maeda: Talanta 48, 705-710 (1999). (d) J.S. Kim, A. Ohki, M.H. Cho, J.K. Kim, D.Y. Ra, N. S. Cho, R.A. Bartsch, K.W. Lee, and W.Z. Oh: Bull. Kor. Chem. Soc. 18, 1014 (1997). (e) J.S. Kim, W.K. Lee, D.Y. Ra, Y.I. Lee, W.K. Choi, K.W. Lee, and W.Z. Oh: Microchem. J. 59, 464 (1998). (f) J.S. Kim, J.H. Pang, I.Y. Yu, W.K. Lee, I.H. Suh, J.K. Kim, M.H. Cho, E.T. Kim, and D.Y. Ra: J. Chem. Soc. Perkin Trans. 2 837 (1999). (g) Z. Asfari, R. Abidi, F. Arnaud-Neu, and J. Vicens: J. Incl. Phenom. 13, 163 (1992). (h) Z. Asfari, J. Weiss, S. Pappalardo, and J. Vicens: Pure Appl. Chem. 65, 585 (1993). (i) C. Hill, J.-F. Dozol, V. Lamare, H. Rouquette, S. Eymard, B. Tournois, J. Vicens, Z. Asfari, C. Bressot, R. Ungaro and A. Casnati: J. Incl. Phenom. 19, 399 (1994). (j) A. Casnati, R. Ungaro, Z. Asfari, and J. Vicens: In Z. Asfari, V. Böhmer, J. Harrowfield, and J. Vicens (eds.), Calixarenes 2001, Kluwer Academic Publishers, Dordrecht, The Netherlands (2001), pp. 365-684.

    Google Scholar 

  16. P. Thuéry, M. Nierlich, J.C. Bryan, V. Lamare, J.F. Dozol, Z. Asfari, and J. Vicens: J. Chem. Soc., Dalton Trans. 4191 (1997).

  17. P. Thuéry, M. Nierlich, J. Vicens, and B. Masci: Acta Crystallogr., Sect. C 57, 833 (2001).

    Google Scholar 

  18. J. Bouquant, A. Delville, J. Grandjean, and P. Laszlo: J. Am. Chem. Soc. 104, 686-691 (1982).

    Google Scholar 

  19. K.H. No, Y.J. Park, and E.J. Choi: Bull. Korean Chem. Soc. 20, 905 (1999).

    Google Scholar 

  20. R.A. Bartsch, I.W. Yang, E.G. Jeon, W. Walkowiak, and W.A. Charewicz: J. Coord. Chem. 27, 75 (1992).

    Google Scholar 

  21. Kappa-CCD Software, Nonius B.V., Delft, The Netherlands (1998).

  22. Z. Otwinowski and W. Minor: Methods Enzymol. 276, 307 (1997).

    Google Scholar 

  23. G.M. Sheldrick, SHELXS-97 and SHELXL-97, University of Göttingen, Germany (1997).

    Google Scholar 

  24. G.M. Sheldrick, SHELXTL, Version 5.1, Bruker AXS Inc., Madison, WI, USA (1999).

    Google Scholar 

  25. Enraf-Nonius, Structure Determination Package, Nonius B.V., Delft, The Netherlands (1994).

  26. G.M. Sheldrick: SHELXS86. Acta Cryst. A46, 467 (1990).

    Google Scholar 

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Correspondence to Jong S. Kim.

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No, K., Chung, H.J., Yu, H.J. et al. 1,3-Alternate and C-1,2-Alternate Tetrahomodioxacalix[4]crowns. Crystal Structures and Metal Ion Complexation. Journal of Inclusion Phenomena 46, 97–103 (2003). https://doi.org/10.1023/A:1025672102973

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