Unexpected racemization behavior of 8,8'-dialkyl-1,1'biisoquinoline

Tetrahedron Asymmetry

Volumn 10, Issue 15, 1999, Pages 2975-2981

  Tsue, Hirohito ^a   Fujinami, Hideyuki ^a   Itakura, Takeshi ^a   Hirao, Ken Ichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; FUNCTIONAL GROUP; ISOQUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ISOMERISM; MOLECULAR STABILITY; PRIORITY JOURNAL; RACEMIC MIXTURE; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0033618605     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00305-5     Document Type: Article

References (21)

1. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley & Sons: New York, 1994; Chapter 14.5.
2. Oki, M. The Chemistry of Rotational Isomers; Springer-Verlag: Berlin, 1993; Chapter 3.
3. Cooke, A. S.; Harris, M. M. J. Chem. Soc. 1963, 2365.
4. Badar, Y.; Cooke, A. S.; Harris, M. M. J. Chem. Soc. 1965, 1412.
5. Cooke, A. S.; Harris, M. M. J. Chem. Soc. C 1967, 988.
6. Kress, R. B.; Duesler, E. N.; Etter, M. C.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1980, 102, 7709.
7. Colter, A. K.; Clements, L. M. J. Phys. Chem. 1964, 68, 651.
8. Tani, K.; Yamagata, T.; Otsuka, S.; Akutagawa, S.; Kumobayashi, H.; Taketomi, T.; Takaya, H.; Miyashita, A.; Noyori, R. Asymmetric Reactions and Processes in Chemistry; Eliel, E. L.; Otsuka, S., Eds. ACS Symposium Series 185. American Chemical Society: Washington, DC, 1982; p. 187.
9. Hayashi, T.; Tomioka, K.; Yonemitsu, O. Asymmetric Synthesis; Kodansha: Tokyo, 1998.
10. Crawford, M.; Smyth, I. F. B. J. Chem. Soc. 1954, 3464.
11. Fujii, M.; Honda, A. J. Heterocycl. Chem. 1992, 29, 931.
12. Fujii, M.; Honda, A. Chem. Express 1992, 7, 329.
13. Hirao, K.; Tsuchiya, R.; Yano, Y.; Tsue, H. Heterocycles 1996, 42, 415.
14. Tsue, H.; Fujinami, H.; Itakura, T.; Tsuchiya, R.; Kobayashi, K.; Takahashi, H.; Hirao, K. Chem. Lett. 1999, 17.
15. Chelucci, G.; Cabras, M. A.; Saba, A.; Sechi, A. Tetrahedron: Asymmetry 1996, 7, 1027.
16. Tsue, H.; Fujinami, H.; Itakura, T.; Hirao, K., unpublished results.
17. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209.
18. Nakamura, M.; Oki, M.; Nakanishi, H.; Yamamoto, O. Bull. Chem. Soc. Jpn. 1974, 47, 2415.
19. Fuji, K.; Sakurai, M.; Tohkai, N.; Kuroda, A.; Kawabata, T.; Fukazawa, Y.; Kinoshita, T.; Toda, T. J. Chem. Soc., Chem. Commun. 1996, 1609.
20. Kranz, M.; Clark, T.; Schleyer, P. von R. J. Org. Chem. 1993, 58, 3317.
21. Ashby, M. T.; Govindan, G. N.; Grafton, A. K. J. Am. Chem. Soc. 1994, 116, 4801.