Experimental and theoretical investigations of absolute stereochemistry and chiroptical properties of enantiopure 2,2′-substituted 9,9′-bianthryls

Tetrahedron Asymmetry

Volumn 14, Issue 12, 2003, Pages 1623-1629

  Toyota, Shinji ^a   Shimasaki, Toshiaki ^a   Tanifuji, Naoki ^a   Wakamatsu, Kan ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; CARBROMAL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; QUINIDINE;

ARTICLE; CALCULATION; CHIRALITY; CIRCULAR DICHROISM; ISOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; ULTRAVIOLET SPECTROSCOPY; X RAY ANALYSIS;

EID: 0038544140     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00252-0     Document Type: Article

References (25)

1. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley: New York, 1994; Chapter 13.
2. Mason S.F., Seal R.H., Roberts D.R. Tetrahedron. 30:1974;1671-1682.
3. Seno K., Hagishita S., Sato T., Kuriyama K. J. Chem. Soc., Perkin Trans. 1. 1984;2013-2022.
4. Badger G.M., Jefferies P.R., Kimber R.W.L. J. Chem. Soc. 1957;1837-1841.
5. Koulotas C., Schwartz L.H. J. Chem. Soc., Chem. Commun. 1969;1400-1400.
6. Badger G.M., Drewer R.J., Lewis G.E. J. Chem. Soc. 1962;4268-4271.
7. Czarniecki S. J. Mol. Struct. 47:1978;365-370.
8. Exciton coupling theory, for example, see: Nakanishi K.; Berova, N. In Circular Dichroism: Principles and Applications; Nakanishi K.; Berova, N.; Woody, R. W., Ed.; VCH: New York, 1994; Chapter 13.
9. Grimme S. Chem. Phys. Lett. 259:1996;128-137.
10. Grimme S., Harren J., Sobanski A., Vögtle F. Eur. J. Org. Chem. 1998;1491-1509.
11. Furche F., Ahlrichs R., Wachsmann C., Weber E., Sobanski A., Vögtle F., Grimme S. J. Am. Chem. Soc. 122:2000;1717-1724.
12. Dastidar, P.; Goldberg, I. In Comprehensive Supramolecular Chemistry; Atwood, J. L.; Davies, J. E. D.; MacNicol, D. D.; Vögtle, F., Ed.; Pergamon: Oxford, 1996; Vol. 6, Chapter 10.
13. Weber E., Ahrendt J., Czugler M., Csöregh I. Angew. Chem., Int. Ed. Engl. 25:1986;746-748.
14. Toda F., Tanaka K., Fujiwara T. Angew. Chem., Int. Ed. Engl. 29:1990;662-664.
15. Schwartz L.H., Koukotas C., Kukkola P., Yu C.S. J. Org. Chem. 51:1986;995-999.
16. Barton D.H.R., Lacher B., Zard S.Z. Tetrahedron. 43:1987;4321-4328.
17. Barton D.H.R., Ferreira J.A. Tetrahedron. 52:1996;9347-9366.
18. Becker H.-D., Langer V., Sieler J., Becker H.-C. J. Org. Chem. 57:1992;1883-1887.
19. Pople J.A., Beveridge D.L., Dobosh P.A. J. Chem. Phys. 47:1967;2026-2033.
20. Ridley J., Zerner M.C. Theoret. Chim. Acta. 32:1973;111-134.
21. For a recent example of the application of ZINDO method to CD calculation, see: Ankai E., Sakakibara K., Uchida S., Yokoyama Y., Yokoyama Y. Bull. Chem. Soc. Jpn. 74:2001;1101-1108.
22. Bringmann G., Kraus J., Schmitt U., Puder C., Zeeck A. Eur. J. Org. Chem. 2000;2729-2734.
23. Barnett E.D.B., Wiltshire J.L. J. Chem. Soc. 1928;1822-1825.
24. Utz C.G., Chechter H. J. Org. Chem. 50:1985;5705-5709.
25. Gaussian 98 (Revision A.9): Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A.; Gaussian, Inc.: Pittsburgh, PA, USA, 1998.