Diastereomers of a cofacial ternaphthalene and two azaternaphthalenes. Syntheses and barriers to isomerization

Tetrahedron

Volumn 53, Issue 15, 1997, Pages 5379-5388

  Zoltewicz, John A ^a   Maier, Norbert M ^a   Lavieri, Sophie ^a   Ghiviriga, Ion ^a   Abboud, Khalil A ^a   Fabian, Walter M F ^b  

^a University of Florida ^*  (United States)

^b UNIVERSITY OF GRAZ   (Austria)

Author keywords

AM1 and PM3 energies; Restricted rotation; X ray structure

Indexed keywords

NAPHTHALENE DERIVATIVE;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOISOMERISM; X RAY ANALYSIS;

EID: 0030891403     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00232-9     Document Type: Article

References (26)

1. Zoltewicz, J. A.; Maier, N. M.; Fabian, W. M. F. Tetrahedron 1996, 52, 8703.
2. Zoltewicz, J. A.; Maier, N. M.; Fabian, W. M. F. J. Org. Chem. submitted.
3. Ibuki, E.; Ozasa, S.; Fujioka, Y.; Hiroshi, M. Chem. Pharm. Bull. 1981, 29, 2103.
4. Kuroda, M.; Nakayama, J.; Hoshino, M.; Furusho, N.; Kawata, T.; Ohba, S. Tetrahedron 1993, 49, 3735.
5. Yarbroff, D.; Branch, G. E. K.; Bettman, B. J. Am. Chem. Soc. 1934, 56, 1850.
6. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
7. Ibuki, E.; Ozasa, S.; Fujioka, Y.; Mizutani, H. Bull. Chem. Soc., Jpn. 1982, 55, 845.
8. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron:Asymmetry 1993, 4, 743.
9. Sanders, G. M.; v.Dijk, M.; den Hertog, H. J. Rec. Trav. Chim. Pays-Bas 1974, 273.
10. Ishikura, M.; Oda, I.; Terashima, M. Heterocycles 1987, 26, 1603.
11. Tsuki, R.; Komatsu, K.; Takeuchi, K.; Shiro, M.; Cohen, S.; Rabinovitz, M. J. Phys. Org. Chem. 1993, 6, 435.
12. Wahl, P.; Krieger, C.; Schweitzer, D.; Staab, H. A. Chem. Ber. 1984, 117, 260.
13. Clough, R. L.; Roberts, J. D. J. Am. Chem. Soc. 1976, 98, 1018.
14. Reetz, M. T.; Breinbauer, R.; Wanninger, K. Tetrahedron Lett. 1996, 37, 4499.
15. Zhang, H. C.; Chan, K. S. Tetrahedron Lett. 1996, 37, 1043.
16. Lorand, J. P.; Edwards, J. O. J. Org. Chem. 1959, 24, 769.
17. Ishikura, M.; Mano, T.; Oda, I.; Terashima, M. Heterocycles 1984, 22, 2471.
18. Sugihara, Y.; Takakura, K.; Murafuji, T.; Miyatake, R.; Nakasuji, K.; Kato, M.; Yano, S. J. Org. Chem. 1996, 61, 6829
19. Murafuji, T.; Mouri, R.; Sugihara, Y.; Takakura, K.; Mikata, Y.; Yano, S. Tetrahedron 1996, 52, 13933.
20. Farina, V. Pure Appl. Chem. 1996, 68, 73.
21. Yamamoto, Y.; Yanagi, A. Chem Pharm. Bull. 1982, 30, 1731.
22. Pedersen, J. R. Acta Chem. Scand. 1972, 26, 929.
23. Kranz, M.; Clark, T.; Schleyer, P. R. J. Org. Chem. 1993, 58, 3317.
24. Sheldrick, G. M. 1995, SHELXTL5, Siemens Analytical Instrumentation, Madison, WS.
25. Dewar, M. J. S.; Zoebisch, E. G.; Healey, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
26. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209.