Enantiomerically pure chiral phenazino-crown ethers: Synthesis, preliminary circular dichroism spectroscopic studies and complexes with the enantiomers of 1-arethyl ammonium salts

Tetrahedron Asymmetry

Volumn 10, Issue 14, 1999, Pages 2775-2795

  Samu, Erika ^a   Huszthy, Péter ^b   Somogyi, László ^c   Hollósi, Miklós ^c  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^c EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; CROWN ETHER DERIVATIVE; LIGAND; PERCHLORATE; PHENAZINE; PHENAZINE DERIVATIVE;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; CYCLIZATION; ENANTIOMER; MOLECULAR RECOGNITION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033575357     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00287-6     Document Type: Article

References (34)

1. (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 2495.
2. (b) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017.
3. (a) Host-Guest Complex Chemistry - I. Topics in Current Chemistry; Springer-Verlag: Berlin, 1981; Vol. 98.
4. (b) Host-Guest Complex Chemistry - II. Topics in Current Chemistry; Springer-Verlag: Berlin, 1982; Vol. 101.
5. Lehn, J. M. Supramolecular Chemistry; VCH: Weinheim, 1995.
6. Lehn, J. M.; Atwood, J. L.; Davies, J. E.; MacNicol, D. D., Eds.; Comprehensive Supramolecular Chemistry; Pergamon: New York, 1996.
7. Stoddart, J. F. Topics in Stereochemistry; Wiley-Interscience: New York, 1988; Vol. 17, pp. 207-288.
8. Izatt, R. M.; Zhu, C. Y.; Huszthy, P.; Bradshaw, J. S. Enantiomeric Recognition in Macrocycle-Primary Ammonium Cation Systems. In Crown Compounds: Toward Future Applications; Cooper, S. R., Ed.; VCH: New York, 1992; Chapter 12.
9. Izatt, R. M.; Wang, T. M.; Hathaway, J. K.; Zhang, X. X.; Curtis, J. C.; Bradshaw, J. S.; Zhu, C. Y.; Huszthy, P. J. Incl. Phenom. 1994, 17, 157.
10. Zhang, X. X.; Bradshaw, J. S.; Izatt, R. M. Chem. Rev. 1997, 97, 3313.
11. Redd, J. T.; Bradshaw, J. S.; Huszthy, P.; Izatt, R. M.; Dalley, N. K. J. Heterocycl Chem. 1998, 35, 1.
12. Wang, T. M., Bradshaw, J. S.; Huszthy, P.; Kou, X.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1994, 31, 1.
13. Huszthy, P.; Samu, E.; Vermes, B.; Mezey-Vándor, G.; Nógrádi, M.; Bradshaw, J. S.; Izatt, R. M. Tetrahedron, 1999, 55, 1491.
14. Gérczei, T.; Böcskei, Z.; Keserû, G. M.; Samu, E.; Huszthy, P. Tetrahedron: Asymmetry 1999, 10, 1995-2005.
15. Bradshaw, J. S.; Huszthy, P.; Wang, T. M.; Zhu, C. Y.; Nazarenko, A. Y.; Izatt, R. M. Supramolecular Chem. 1993, 1, 267.
16. Huszthy, P.; Bradshaw, J. S.; Bordunov, A. V.; Izatt, R. M. ACH - Models in Chemistry 1994, 131, 445.
17. Köntös, Z.; Huszthy, P.; Bradshaw, J. S.; Izatt, R. M. Tetrahedron: Asymmetry 1999, 10, 2087-2099.
18. Jones, B. A.; Bradshaw, J. S.; Izatt, R. M. J. Heterocycl. Chem. 1982, 19, 551.
19. Otomasu, H. Chem. Pharm. Bull. 1955, 5, 365.
20. Bradshaw, J. S.; Huszthy, P.; McDaniel, C. W.; Zhu, C. Y.; Dalley, N. K.; Izatt, R. M. J. Org. Chem. 1990, 55, 3129.
21. Mori, K.; Chiba, N. Liebigs Ann. Chem. 1989, 957.
22. Huszthy, P.; Bradshaw, J. S.; Zhu, C. Y.; Izatt, R. M.; Lifson, S. J. Org. Chem. 1991, 56, 3330.
23. Huszthy, P.; Oue, M.; Bradshaw, J. S.; Zhu, C. Y.; Wang T. M.; Dalley, N. K.; Curtis, J. C.; Izatt, R. M. J. Org. Chem. 1992, 57, 5383.
24. Curl, R. F. J. Chem. Phys. 1959, 30, 1529.
25. (a) Harada, N.; Nakanishi, K. Circular Dichroism Spectrosopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983; Chapter 12.
26. (b) Nakanishi, K.; Berova, N. Circular Dichroism. Principles and Applications; Nakanishi, K.; Berova, N.; Woody, R. W., Eds.; VCH, 1994; Chapter 13, pp. 361-398.
27. (a) Somogyi, L.; Huszthy, P.; Bradshaw, J. S.; Izatt, R. M.; Hollósi, M. Chirality 1997, 9, 545.
28. (b) Somogyi, L.; Huszthy, P.; Köntös, Z.; Hollósi, M. Enantiomer 1998, 3, 439.
29. Harada, N.; Tamai, Y.; Takuma, Y.; Uda, H. J. Am. Chem. Soc. 1980, 102, 501.
30. Rosini, C.; Ruzziconi, R.; Suporchi, S.; Fringuelli, E.; Piermatti, O. Tetrahedron: Asymmetry 1998, 9, 55.
31. Riddick, J. A.; Burger, W B. Organic Solvents in Techniques of Organic Chemistry, 3rd ed.; Weissberger, A., Ed.; Wiley-Interscience: New York, 1970; Vol. II.
32. Rautio, M. Acta Chem. Scand. 1979, B33, 770.
33. Lettré, H.; Wölcke, U. Liebigs Ann. Chem. 1967, 705, 75.
34. Mori, K. Tetrahedron 1976, 32, 1101.