Abstract
A number of new 15- and 1 8-membered ring aza-crown (4, 5, 8–13, 17, 18) and lariat ethers (6, 7) incorporating glucose or galactose units have been synthesized in good yields by a simple route. Their extracting abilities were measured with Li+, Na+, K+ and NH +4 cations. The substituents at the nitrogen atom and the type of monosaccharide affected this property significantly.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
D. A. H. van Maarschalkerwaart, N. P. Willard, and U. K. Pandit:Tetrahedron 48, 8825 (1992).
E. V. Dehmlow and V. Knufinke:Liebigs Ann. Chem. 282 (1992).
M. J. O'Donnell:Asymmetric Phase Transfer Reactions in Catalytic Asymmetric Synthesis (Ed.: I. Ojima) VCH Publishers, Inc., New York-Weinheim-Cambridge, pp. 367–387 (1993).
T. Wang, J. S. Bradshaw, P. Huszthy, X. Kou, N. K. Dalley, and R. M. Izatt:J. Heterocyclic Chem. 31, 1 (1994).
J. F. Stoddart:Chem. Soc. Rev. 8, 85 (1979)
J. F. Stoddart:Synthetic Chiral Receptor Molecules from Natural Products (Progress in Macrocycles Chemistry, Vol. 2, Ed. R. M. Izatt and J. J. Christensen), p. 173, Wiley (1981).
J. F. Stoddart:Chiral Crown Ethers (Topics in Stereochemistry, Vol. 17, Ed. E. L. Eliel and S. H. Wielen), p. 207, Wiley (1988).
D. A. Laidler and J. F. Stoddart:J. Chem. Soc., Chem Commun. 979 (1976).
H. F. Beckford, R. M. King, J. F. Stoddart, and R. F. Newton:Tetrahedron Lett. 171 (1978).
M. Pietraszkiewicz and J. Jurczak:Tetrahedron 40, 2967 (1984).
M. Pietraszkiewicz, P. Salanski, and J. Jurczak:Tetraheron 40, 2971 (1984).
G. Tóth, W. Dietrich, P. Bakó, L. Fenichel, and L. Töke:Carbohydr. Res. 168, 141 (1987).
P. Bakó, L. Fenichel, L. Töke, and B. E. Davison:J. Chem. Soc. Perkin Trans. 1 1235 (1990).
P. Bakó, L. Fenichel, and L. Töke:Liebigs Ann. Chem. 1161 (1990).
G. W. Gokel:Chem. Soc. Rev. 21, 39 (1992) and references therein.
M. Zinic, S. Alihodzic, and Skaric:J. Chem Soc. Perkin Trans. 1 21 (1993).
M. Zinic, L. Frkanec, V. Skarin, Y. Trafton, and G. W. Gokel:J. Chem. Soc. Chem. Commun. 1726 (1990).
P. Di Cesare and B. Gross:Synth. Commun. 4581 (1979).
K. Kimura, T. Maeda, and T. Shono:Talanta 26, 945 (1979).
T. Maeda, K. Kimura, and T. Shono:Bull. Chem. Soc. Jpn. 55, 3506 (1982).
D. A. Laidlerl and J. F. Stoddart:Carbohydr. Res. 55, C1 (1977).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Bakó, P., Töke, L. Novel monoaza- and diazacrown ethers incorporating sugar units and their extraction ability towards picrate salts. J Incl Phenom Macrocycl Chem 23, 195–201 (1995). https://doi.org/10.1007/BF00709577
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00709577