New functional hexahelicenes - Synthesis, chiroptical properties, X-ray crystal structures, and comparative data bank analysis of hexahelicenes

European Journal of Organic Chemistry

Volumn , Issue 15, 2003, Pages 2863-2876

  Wachsmann, Claudia ^a   Weber, Edwin ^a   Czugler, Mátyás ^b   Seichter, Wilhelm ^a  

^a TU BERGAKADEMIE FREIBERG   (Germany)

^b CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

Chiroptical properties; Circular dichroism; Helicenes; Pi interactions; Supramolecular chemistry

Indexed keywords

1,1' (HEXAHELICENE 2,15 DIYL)DIMETHANOL; 1,1,1',1' TETRAKIS(4 METHYLPHENYL) 1,1' (HEXAHELICENE 2,15 DIYL)DIMETHANOL; 1,1,1',1' TETRAPHENYL 1,1' (HEXAHELICENE 2,15 DIYL)DIMETHANOL; ACETONE; BIS(2 METHYLPROPYL)HEXAHELICENE 2,15 DICARBOXYLATE; CHLOROFORM; CYCLOALKENE; DIMETHYLHEXAHELICENE 2,15 DICARBOXYLATE; FUNCTIONAL GROUP; HEXAHELICENE; HEXAHELICENE 2,15 DICARBOXYLIC ACID; HEXAHELICENE 2,15 DIMETHANAMINE; HEXAHELICENE 2,15 DIOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHIRALITY; CIRCULAR DICHROISM; CRYSTAL STRUCTURE; DATA BASE; MOLECULAR WEIGHT; OPTICAL ROTATION; STATISTICAL ANALYSIS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0042656724     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300084     Document Type: Article

References (58)

1. M. S. Newman, D. Lednicer, J. Am. Chem. Soc. 1956, 78, 4765.
2. R. H. Martin, Angew. Chem. 1974, 86, 727; Angew. Chem. Int. Ed. Engl. 1974, 13, 649.
3. R. H. Martin, Angew. Chem. 1974, 86, 727; Angew. Chem. Int. Ed. Engl. 1974, 13, 649.
4. H. Wijnberg, Acc. Chem. Res. 1971, 4, 65.
5. [a] W. H. Laarhoven, W. J. C. Prinsen, in Stereochemistry (Eds.: F. Vögtle, E. Weber), Topics in Current Chemistry, vol. 125, Springer-Verlag, Berlin - Heidelberg, 1984.
6. [b] K. P. Meurer, F. Vögtle, in Organic Chemistry (Ed.: F. L. Boschke), Topics in Current Chemistry, vol. 127, Springer-Verlag, Berlin - Heidelberg, 1985.
7. [c] T. J. Katz, Angew. Chem. 2000, 112, 1997; Angew. Chem. Int. Ed. 2000, 39, 1921.
8. [c] T. J. Katz, Angew. Chem. 2000, 112, 1997; Angew. Chem. Int. Ed. 2000, 39, 1921.
9. E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, New York, 1994.
10. [a] M. Nakazaki, K. Yamamoto, T. Ikeda, T. Kitsuki, Y. Okamoto, J. Chem. Soc., Chem. Commun. 1983, 787.
11. [b] K. Yamamoto, T. Ikeda, T. Kitsuki, Y. Okamoto, H. Chikamatsu, M. Nakazaki, J. Chem. Soc., Perkin Trans. 1 1990, 271.
12. L. Owens, C. Thilgen, F. Diederich, C. B. Knobler, Helv. Chim. Acta 1993, 76, 2757.
13. K. Tanaka, Y. Shogase, H. Osuga, H. Suzuki, W. Nakanishi, K. Nakamura, Y. Kawai, J. Chem. Soc., Chem. Commun. 1995, 1873.
14. A. Terfort, H. Görls, H. Brunner, Synthesis 1997, 79.
15. M. T. Reetz, E. W. Beuttenmüller, R. Goddard, Tetrahedron Lett. 1997, 38, 3211.
16. K. Tanaka, Y. Kitahara, Chem. Commun. 1998, 1141.
17. O. Ermer, J. Neudörfl, Helv. Chim. Acta 2001, 84, 1268.
18. F. Furche, R. Ahlrichs, C. Wachsmann, E. Weber, A. Sobanski, F. Vögtle, S. Grimme, J Am. Chem. Soc. 2000, 122, 1717.
19. [a] R. H. Martin, M. J. Marchant, M. Baes, Helv. Chim. Acta 1971, 54, 358.
20. [b] A. Moradpour, H. Kagan, M. Baes, G. Morren, R. H. Martin, Tetrahedron 1975, 31, 2139.
21. [c] J. M. Brown, I. P. Field, P. J. Sidebottom, Tetrahedron Lett. 1981, 22, 4867.
22. J. H. Borkent, W. H. Laarhoven, Tetrahedron 1978, 34, 2565.
23. H. J. Bestmann, O. Klein, in Methoden Org. Chem., (Houben-Weyl), 1972, vol. V/1b, p. 383.
24. [a] F. B. Mallory, C. W. Mallory, in Org. Reactions, John Wiley & Sons, New York, 1984, vol. 30, p. 1.
25. [b] W H. Laarhoven, Recl. Trav. Chim. Pays-Bas 1983, 102, 185.
26. H. Meier, Angew. Chem. 1992, 104, 1425; Angew. Chem. Int. Ed. Engl. 1992, 31, 1399.
27. H. Meier, Angew. Chem. 1992, 104, 1425; Angew. Chem. Int. Ed. Engl. 1992, 31, 1399.
28. A. Hajos, in Methoden Org. Chem., (Houben-Weyl), 1981, vol. IV/1d, p. 1.
29. [a] B. Yang, L. Liu, T. J. Katz, C. A. Liberko, L. L. Miller, J. Am. Chem. Soc. 1991, 113, 8993.
30. [b] J. F. W. McOmie, M. L. Watts, D. E. West, Tetrahedron 1968, 24, 2289.
31. H. Henecka, in Methoden Org. Chem., (Houben-Weyl), 1952, vol. VIII, p. 359.
32. U. Schöllkopf, in Methoden Org. Chem., (Houben-Weyl), 1970, vol. XIII/1, p. 87.
33. [a] H. Häkli, M. Mintas, A. Mannschreck, Chem. Ber. 1979, 112, 2028.
34. [b] G. Hasse, R. Hagel, Justus Liebigs Ann. Chem. 1976, 996.
35. [a] D. M. Johns, in Chiral Liquid Chromatography, (Ed.: W. J. Lough), Blackie, Glasgow, 1989, p. 116.
36. [b] S. G. Allenmark, Chromatographic Enantioseparation: Methods and Applications, 2nd ed., Ellis Horwood, Chichester, 1991.
37. [a] G. Snatzke, in Methodicum Chimicum, (Ed.: F. Korte), vol. 1A, Thieme, Stuttgart, 1974, chapter 5.7.
38. [b] G. Snatzke, Angew. Chem. 1979, 91, 380; Angew. Chem. Int. Ed. Engl. 1979, 18, 363.
39. [b] G. Snatzke, Angew. Chem. 1979, 91, 380; Angew. Chem. Int. Ed. Engl. 1979, 18, 363.
40. A. Brown, C. M. Kemp, S. F. Mason, J. Chem. Soc., A 1971, 751.
41. M. S. Newman, R. S. Darlak, L. Tsai, J. Am. Chem. Soc. 1967, 89, 6191.
42. (Eds.: J. Jaques, A. Collet, S. H. Wilen), Enantiomers, Racemates, and Resolutions, John Wiley & Sons, New York, 1981.
43. C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525.
44. G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond, IUCr Monographs on Crystallography, vol. 9, Oxford University Press, Oxford, 1999.
45. M. Nishio, M. Hirota, Y. Umezawa, The CH/π Interaction, John Wiley & Sons, New York, 1998.
46. E. Weber, N. Dörpinghaus, I. Csöregh, J. Chem. Soc., Perkin Trans. 2 1990, 2167.
47. G. R. Desiraju, Crystal Engineering - The Design of Organic Solids, Elsevier, Amsterdam, 1989.
48. [a] J. L. Atwood, F. Hamada, K. D. Robinson, G. W. Orr, R. L. Vincent, Nature 1991, 349, 683.
49. [b] E. Weber, T. Hens, O. Gallardo, I. Csöregh, J. Chem. Soc., Perkin Trans. 2 1996, 737.
50. F. H. Allen, Acta Crystallogr., Sect. B 2002, 58, 380.
51. PREQUEST Manual, online documentation at: http://www.ccdc.cam.ac.uk/support/csddoc/prequest/zprequest.html.
52. VISTA 2,0 Manual, online documentation at: http://www.ccdc.cam.ac.uk/support/csddoc/vista/zvista.html.
53. Independent hits in this context are crystal structures that resulted from independent measurements or are of independent molecules of the asymmetric units. Supporting information for a list of the REFCODEs of the retrieved compounds together with their literature references are deposited and available upon request from either one of the authors (MC), or from the publisher.
54. [a] B. S. Green, M. Knossow, Science (Washington DC) 1981, 214, 795.
55. [b] S. Ramadas, J. M. Thomas, M. E. Jordan, C. J. Eckardt, J. Phys. Chem. 1981, 85, 2421.
56. K. E. S. Phillips, T. J. Katz, S. Jockusch, A. J. Lovinger, N. J. Turro, J. Am. Chem. Soc. 2001, 123, 11899.
57. G. M. Sheldrick, SHELXS-86: Program for Crystal Structure Solution, University of Göttingen, Germany, 1986.
58. G. M. Sheldrick, SHELXS-93: Program for Crystal Structure Refinement, University of Göttingen, Germany, 1993.