Absolute conformation and chiroptical properties. VI. 2,2',3,3'- tetramethoxy-9,9'-bitriptycyl: A stereochemical analog of 1,2-disubstituted ethane with identical substituents

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 11, 1998, Pages 2715-2720

  Toyota, Shinji ^a   Yasutomi, Akihiro ^a   Kojima, Hiroharu ^a   Igarashi, Yuko ^a   Asakura, Mitsuhiro ^a   Oki, Michinori ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,2',3,3' TETRAMETHOXY 9,9' BITRIPTYCYL; ORGANIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CONFORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; METHYLATION; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0031764319     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.2715     Document Type: Article

References (25)

1. For Part V of the series, see Ref. 5.
2. A preliminary note has been published: S. Toyota, A. Yasutomi, and M. Ōki, Tetrahedron Lett., 36, 6297 (1995).
3. S. Toyota, H. Yamane, and M. Ōki, Bull. Chem. Soc. Jpn., 66, 212 (1993).
4. S. Toyota, T. Miyasaka, Y. Matsumoto, T. Matsuo, and M. Ōki, Bull. Chem. Soc. Jpn., 67, 1680 (1994).
5. S. Toyota, T. Akinaga, H. Kojima, M. Aki, and M. Ōki, J. Am. Chem. Soc., 118, 11460 (1996).
6. L. H. Schwartz, C. Koukotus, P. Kukkola, and C. S. Yu, J. Org. Chem., 51, 955 (1986).
7. B. L. Hawkins, W. Bremser, S. Borcic, and J. D. Roberts, J. Am. Chem. Soc., 93, 4472 (1971).
8. S. Brownstein, J. Dunogues, D. Lindsay, and K. U. Ingold, J. Am. Chem. Soc., 99, 2073 (1977); M. A. Falmm-ter Meer, H.-D. Beckhaus, K. Peters, H.-G. von Schnering, H. Fritz, and C. Rüchardt, Chem. Ber., 119, 1492 (1986).
9. S. Brownstein, J. Dunogues, D. Lindsay, and K. U. Ingold, J. Am. Chem. Soc., 99, 2073 (1977); M. A. Falmm-ter Meer, H.-D. Beckhaus, K. Peters, H.-G. von Schnering, H. Fritz, and C. Rüchardt, Chem. Ber., 119, 1492 (1986).
10. W. Keely and J. S. Shannon, Aust. J. Chem., 13, 103 (1960).
11. D. W. Cameron and P. E. Schüts, J. Chem. Soc. C, 1967, 2121.
12. G. I. Feutrill and R. N. Mirrington, Tetrahedron Lett., 1970, 1327; G. I. Feutrill and R. N. Mirrington, Aust. J. Chem., 25, 1719 (1972); G. I. Feutrill and R. N. Mirrington, Aust. J. Chem., 25, 1731 (1972).
13. G. I. Feutrill and R. N. Mirrington, Tetrahedron Lett., 1970, 1327; G. I. Feutrill and R. N. Mirrington, Aust. J. Chem., 25, 1719 (1972); G. I. Feutrill and R. N. Mirrington, Aust. J. Chem., 25, 1731 (1972).
14. G. I. Feutrill and R. N. Mirrington, Tetrahedron Lett., 1970, 1327; G. I. Feutrill and R. N. Mirrington, Aust. J. Chem., 25, 1719 (1972); G. I. Feutrill and R. N. Mirrington, Aust. J. Chem., 25, 1731 (1972).
15. N. Harada, T. Nehira, T. Soutome, N. Hiyoshi, and F. Kido, Enantiomer, 1, 35 (1996).
16. A. Kiss, J. Molnár, and C. Sándorfy, Compt. Rend., 227, 724 (1948).
17. J. de Wit and H. Wynberg, Tetrahedron, 29, 1379 (1973).
18. F. Bell and D. H. Waring, J. Chem. Soc., 1949, 267.
19. K. Lagodzinski, Ber., 28, 116 (1895); K. Lagodzinski, Justus Liebigs Ann. Chem., 342, 90 (1905).
20. K. Lagodzinski, Ber., 28, 116 (1895); K. Lagodzinski, Justus Liebigs Ann. Chem., 342, 90 (1905).
21. W. Hückel, O. Neunhoeffer, A. Gerke, and E. Frank, Justus Liebigs Ann. Chem., 477, 99 (1930); R. S. Topson, M. A. Clapp, and L. H. Cretcher, J. Org. Chem., 12, 133 (1947); S. Winstein, F. Grunwald, R. E. Buckles, and C. Hanson, J. Am. Chem. Soc., 70, 816 (1948).
22. W. Hückel, O. Neunhoeffer, A. Gerke, and E. Frank, Justus Liebigs Ann. Chem., 477, 99 (1930); R. S. Topson, M. A. Clapp, and L. H. Cretcher, J. Org. Chem., 12, 133 (1947); S. Winstein, F. Grunwald, R. E. Buckles, and C. Hanson, J. Am. Chem. Soc., 70, 816 (1948).
23. W. Hückel, O. Neunhoeffer, A. Gerke, and E. Frank, Justus Liebigs Ann. Chem., 477, 99 (1930); R. S. Topson, M. A. Clapp, and L. H. Cretcher, J. Org. Chem., 12, 133 (1947); S. Winstein, F. Grunwald, R. E. Buckles, and C. Hanson, J. Am. Chem. Soc., 70, 816 (1948).
24. S. T. Cristol, D. G. Seapy, and E. O. Aeling, J. Am. Chem. Soc., 105, 7337 (1983).
25. c data, bond lengths, bond angles, torsion angles, and experimental details are deposited as Document No. 71057 at the Office of the Editor of Bull. Chem. Soc. Jpn.