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Chiral Recognition Properties of Chiral 18-Crown-6 Ethers with Aromatic Substituents

  • Conference paper
Clathrate Compounds, Molecular Inclusion Phenomena, and Cyclodextrins

Part of the book series: Advances in Inclusion Science ((AIS,volume 3))

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Abstract

The chiral recognition properties of chiral 18-crown-6 ethers with phenyl, 1-naphthoxymethyl, 1-naphthylmethyl, or 2,3,5,6-tetramethylphenylmethyl substituents for α-phenylglycine methyl ester and 1-phenylethylamine perchlorate were investigated by a standard extraction procedure. The chiral recognition factor of 1-naphthoxymethyl substituted crown ether is 2.0 for the former salt but near 1.0 for the latter, whereas that of the other crown ethers is not so dependent on the structure of salts, which indicates the importance of the mutual relation of the structure of host and guest molecules.

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References

  1. S.T. Jolley, J. S. Bradshaw, and R. M. Izatt, J. Heterocyclic Chem., 19, 3(1982);

    Google Scholar 

  2. M. Nakazaki, K. Yamamoto, T. Ikeda, T. Kitsuki, and Y. Okamoto, J. Chem. Soc., Chem. Commun., 1983, 787;

    Google Scholar 

  3. R. B. Davidson, J. S. Bradshaw, B. A. Jones, N. K. Dalley, J. S. Christensen, and R. M. Izatt, J. Org. Chem., 49, 353(1984), and references cited therein.

    Google Scholar 

  4. J.M. Timko, R. C. Helgeson, M. Newcomb, G. W. Gokel, and D. J. Cram, J. Am. Chem. Soc., 96, 7097 (1974).

    Google Scholar 

  5. Preliminary communication: J. Yamashita, M. Minagawa, A. Sonobe, S Ohashi, M. Kawamura, K. Shimizu, and H. Hashimoto, Chem. Lett., 1982, 1409; A part of this work was presented at The 3rd International Synposium on Clathrate Compounds and Molecular Inclusion Phenomena and The 2nd International Synposium on Cyclodextrin(Abs. No. 1002), Tokyo, Japan, July 24, 1984.

    Google Scholar 

  6. F.Weygand and R. Geiger, Chem. Ber., 89, 647 (1956).

    Google Scholar 

  7. J.Dale and P.0. Kristiansen, Acta. Chem. Scand., 26, 1471 (1972).

    Google Scholar 

  8. D.S. Lingenfelter, R.C. Helgeson, and D. J. Cram, J. Org. Chem., 46, 393 (1981).

    Google Scholar 

  9. L.J. Ruben, H.A. Lardy, and H. O. Fischer, J. Am. Chem. Soc., 74 425 (1952).

    Google Scholar 

  10. G.Berti and F. Bottari, J. Org. Chem., 25, 1286 (1959).

    Google Scholar 

  11. A.Collet, Synthesis, 1973, 664.

    Google Scholar 

  12. D.Roach and C.W. Gehrke, J. Chromatogr., 44, 269 (1969).

    Google Scholar 

  13. S.S. Peacock, D.M. Walba, F. C. A. Gaeta, R. C. Helgeson, and D. J. Cram, J. Am. Chem. Soc., 102, 2043 (1980).

    Google Scholar 

  14. W.H. Pirkle, D.W. House, and J. M. Finn, J. Chromatogr., 192, 143 (1980).

    Google Scholar 

  15. K.Kruse, W. Francke, and W. A. Koenig,J Chromatogr., 170, 423 (1979).

    Google Scholar 

  16. S.C. Peacock, L.A. Domeier, F. C. A. Gaeta, R. C. Helgeson, J. M Timko, D. J. Cram, J. Am. Chem. Soc., 100, 8190 (1978).

    Google Scholar 

  17. W.S. Curtis, D.A. Laidler, J. F. Stoddart, and G. H. Jones, J. Chem. Soc., Perkin I,1977, 1756;

    Google Scholar 

  18. W. Bussman, J.M. Lehn, U. Oesch P. Plumere, and W. S. Simmon, Helv. Chim. Acta., 64, 657 (1981).

    Google Scholar 

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© 1984 D. Reidel Publishing Company

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Yamashita, J., Takahashi, H., Hashimoto, H., Kitahara, K., Sato, H. (1984). Chiral Recognition Properties of Chiral 18-Crown-6 Ethers with Aromatic Substituents. In: Atwood, J.L., Davies, J.E.D., Osa, T. (eds) Clathrate Compounds, Molecular Inclusion Phenomena, and Cyclodextrins. Advances in Inclusion Science, vol 3. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-5376-5_14

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  • DOI: https://doi.org/10.1007/978-94-009-5376-5_14

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-8872-5

  • Online ISBN: 978-94-009-5376-5

  • eBook Packages: Springer Book Archive

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