Chiral N-(o-aryl)-thiazolidinediones: Synthesis from rhodanines and investigation on rotational enantiomers by NMR spectroscopy

Canadian Journal of Chemistry

Volumn 76, Issue 3, 1998, Pages 254-259

  Karataş, Mehmet ^a   Koni, Serap ^a   Dogǎn, Ilknur ^a  

^a BOGAZICI UNIVERSITY   (Turkey)

Author keywords

1H and 13C NMR; Chiral auxiliary; Chirality; N (o aryl) 2,4 thiazolidinediones; N (o aryl) rhodanines; Rotational isomerism

Indexed keywords

AROMATIC COMPOUNDS; CONFORMATIONS; ELECTRON ENERGY LEVELS; FLUORINE COMPOUNDS; HYDROGEN BONDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTONS; SYNTHESIS (CHEMICAL);

ARYL THIAZOLIDINEDIONES; ENANTIOMERS; RHODANINES;

SULFUR COMPOUNDS;

EID: 0032025833     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/cjc-76-3-254     Document Type: Article

References (22)

1. P.H. Bird, L.D. Colebrook, A.R. Fraser, and H.G. Giles. J. Chem. Soc Chem. Commun. 225 (1974).
2. L.D. Colebrook and H.G. Giles. Can. J. Chem. 51, 3635 (1972).
3. L.D. Colebrook and H.G. Giles. Tetrahedron Lett. 5239 (1972).
4. L.D.Colebrook and H.G. Giles. Can. J. Chem. 53, 3431 (1975).
5. A. Djafri, C. Roussel, and J. Sandström. J. Chem. Soc. Perkin Trans. 2, 273 (1985).
6. W.H. Pirkle. J. Am. Chem. Soc. 88, 1837 (1966).
7. A. Mannschreck, V. Jonas, and B. Kolb. Angew. Chem. 12, 583 (1973).
8. C. Kashima, A. Katoh, Y. Omote, and Y. Nakata. Heterocycles, 9, 469 (1978).
9. M. Mintas, Z. Orhanovic, K. Jakopcic, H. Kohler, G. Stuhler, and A. Mannschreck. Tetrahedron, 41, 229 (1985).
10. C. Roussel and A. Djafri. New J. Chem. 10, 399 (1986).
11. C. Roussel and A. Chemlal. J. Chromatogr. 95, 462 (1989).
12. C. Roussel, J. Stein, and L. Beauvais. New J. Chem. 169 (1990).
13. L.D. Colebrook. Can. J. Chem. 69, 1957 (1991).
14. İ. Dogan, T. Burgemeister, S. İçli, and A. Mannschreck. Tetrahedron, 48, 7157 (1992).
15. İ. Doǧan, N. Pustet, and A. Mannschreck. J. Chem. Soc. Perkin Trans. 2, 1557 (1993).
16. C. Roussel, M. Adjimi, A. Chemlal, and A. Djafri. J. Org. Chem. 53, 5076 (1988).
17. J. Vorcapic'-Furac', M. Mintas, T. Burgemeister, and A. Mannschreck. J. Chem. Soc. Perkin Trans. 2, 713 (1989).
18. M. Mintas, V. Mihaljevic', H. Koller, D. Schuster, and A. Mannschreck. J. Chem. Soc. Perkin Trans. 2, 619 (1990).
19. R. Sarac-Arneri, M. Mintas, N. Pustet, and A. Mannschreck. Monatsh. Chem. 125, 457 (1994).
20. I.A. Vogel. In Practical organic chemistry. 4th ed. Wiley, New York. 1978. p. 736.
21. L.D. Colebrook, S. İçli, and F.H. Hund. Can. J. Chem. 53, 1556 (1975).
22. M.T. Omar. Bull. Chem. Soc. Jpn. 64, 750 (1991).