Optically active aromatics possessing helical chirality: One-pot synthesis, optical resolution and crystal structure of 13,14-dimethyldibenzo[b,j][4,7]phenanthroline and its dihydro form as a novel chiral building block

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 16, 1998, Pages 2471-2472

  Tanaka, Yasutaka ^a,b   Sekita, Akemi ^b   Suzuki, Hiroshi ^b   Yamashita, Mitsuji ^b   Oshikawa, Tatsuo ^b   Yonemitsu, Tadashi ^c   Torii, Akiyoshi ^d  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b SHIZUOKA UNIVERSITY   (Japan)

^c KYUSHU SANGYO UNIVERSITY   (Japan)

^d KURUME NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748646177     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a805076g     Document Type: Article

References (15)

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4. R. H. Martin, Angew. Chem., Int. Ed. Engl., 1974, 13, 649;
5. H. Wynberg, Acc. Chem. Res., 1971, 4, 65.
6. For recent reports of helical chirality see K. Tanaka, H. Osuga, H. Suzuki, Y. Shogase and Y. Kitahara, J. Chem. Soc., Perkin Trans. 1, 1998, 935;
7. K. Kano, S. Negi, H. Kamo, T. Kitae, M. Yamaguchi, H. Okubo and M. Hirama, Chem. Lett., 1998, 151;
8. M. Yamaguchi, H. Okubo and M. Hirama, Chem. Commun., 1996, 1771 and references cited therein.
9. For phenanthrene derivatives analogous to 1 see K. Mislow, R. Graeve, A. J. Gordon and G. H. Wahl, Jr., J. Am. Chem. Soc., 1964, 86, 1733;
10. R. N. Armstrong, H. L. Ammon and J. N. Darnow, J. Am. Chem. Soc., 1987, 109, 2077.
11. A. Bernthsen, Ann., 1884, 224, 1.
12. J. Jacques and C. Fouquey, Org. Synth., 1989, 67, 1.
13. In Fig. 2 the CD bands at 263.5 and 210 nm are first and second Cotton effects, respectively, which are determined by CD and UV-VIS Spectra of 2. Excitation-coupled CD is based on interacting chromophores, in 2 two quinoline moieties. When the two chromophores are oriented with clockwise movement from front to back the sign of first CD is positive and when anti-clockwise the sign of first CD is negative, see N. Harada and K. Nakanishi, J. Am. Chem. Soc., 1969, 91, 2989;
14. Circular Dichroism, Principles and Applications, ed. K. Nakanishi, N. Berova and R. Woody, VCH Publishers, 1994.
15. C. de Rango, G. Tsoucaris, J. P. Declercq, G. Germain and J. P. Putzeys, Cryst. Struct. Commun., 1973, 2, 189.