Conformational anaysis in solution of C2-symmetric 1,1'-binaphthyl derivatives by circular dichroism spectroscopy and cholesteric induction in nematic mesophases

Journal of Organic Chemistry

Volumn 65, Issue 18, 2000, Pages 5522-5527

  Proni, Gloria ^a,c   Spada, Gian Piero ^a   Lustenberger, Philipp ^b   Welti, Roger ^b   Diederich, François ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b ETH ZURICH   (Switzerland)

^c NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE; NAPHTHALENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHIRALITY; CONFORMATION; ENANTIOMER;

EID: 0033832988     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0001683     Document Type: Article

References (63)

1. Noyori, R. In Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Hattori, T.; Goto, J.; Miyano, S. J. Synth. Org. Chem. Jpn. 1992, 50, 986. Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503. Reiser, O. Nachr. Chem. Technol. Lab. 1996, 44, 380. Pu, L. Chem. Rev. 1998, 98, 2405.
2. Noyori, R. In Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Hattori, T.; Goto, J.; Miyano, S. J. Synth. Org. Chem. Jpn. 1992, 50, 986. Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503. Reiser, O. Nachr. Chem. Technol. Lab. 1996, 44, 380. Pu, L. Chem. Rev. 1998, 98, 2405.
3. Noyori, R. In Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Hattori, T.; Goto, J.; Miyano, S. J. Synth. Org. Chem. Jpn. 1992, 50, 986. Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503. Reiser, O. Nachr. Chem. Technol. Lab. 1996, 44, 380. Pu, L. Chem. Rev. 1998, 98, 2405.
4. Noyori, R. In Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Hattori, T.; Goto, J.; Miyano, S. J. Synth. Org. Chem. Jpn. 1992, 50, 986. Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503. Reiser, O. Nachr. Chem. Technol. Lab. 1996, 44, 380. Pu, L. Chem. Rev. 1998, 98, 2405.
5. Noyori, R. In Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Hattori, T.; Goto, J.; Miyano, S. J. Synth. Org. Chem. Jpn. 1992, 50, 986. Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503. Reiser, O. Nachr. Chem. Technol. Lab. 1996, 44, 380. Pu, L. Chem. Rev. 1998, 98, 2405.
6. Noyori, R. In Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Hattori, T.; Goto, J.; Miyano, S. J. Synth. Org. Chem. Jpn. 1992, 50, 986. Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503. Reiser, O. Nachr. Chem. Technol. Lab. 1996, 44, 380. Pu, L. Chem. Rev. 1998, 98, 2405.
7. (a) Kyba, E. P.; Siegel, M. G.; Sousa, L. R.; Sogah, G. D. Y.; Cram, D. J. J. Am. Chem. Soc. 1973, 95, 2691.
8. (b) Kyba, E. B.; Koga, K.; Sousa, L. R.; Siegel, M. G.; Cram, D. J. J. Am. Chem. Soc. 1973, 95, 2692.
9. (c) Peacock, S. C.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1976, 282.
10. (d) Diederich, F.; Hester, M. R.; Uyeki, M. A. Angew. Chem., Int. Ed. Engl. 1988, 27, 1705.
11. (e) Castro, P. P.; Georgiadis, T. M.; Diederich, F. J. Org. Chem. 1989, 54, 5835.
12. (f) Hester, M. R.; Uyeki, M. A.; Diederich, F. Isr. J. Chem. 1989, 29, 201.
13. (g) Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596.
14. (h) Martinborough, E.; Mordasini Denti, T.; Castro, P. P.; Wyman, T. B.; Knobler, C. B.; Diederich, F. Helv. Chim. Acta 1995, 78, 1037.
15. (i) Takeuchi, M.; Yoda, S.; Imada, T.; Shinkai, S. Tetrahedron 1997, 53, 8335.
16. (j) Sudo, Y.; Yamaguchi, T.; Shinbo, T. J. Chromatogr. A 1996, 736, 39.
17. (k) Asakawa, M.; Brown, C. L.; Pasini, D.; Stoddart, J. F.; Wyatt, P. G. J. Org. Chem. 1996, 61, 7234.
18. (l) Asakawa, M.; Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Menzer, S.; Pasini, D.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J.; Wyatt, P. G. Chem. Eur. J. 1997, 3, 463.
19. (m) Kawabata, T.; Kuroda, A.; Nakata, E.; Takasu, K.; Fuji, K. Tetrahedron Lett. 1996, 37, 4153.
20. (n) Garcia-Tellado, F.; Albert, J.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1991, 1761.
21. (o) Kavenova, I.; Holakovsky, R.; Hovorka, M.; Kriz, V.; Anzenbacher, P.; Matejka, P.; Kral, V.; Genge, J. W.; Sessler, J. L. Chem. Listy 1998, 92, 147.
22. (p) Vandoorn, A. R.; Rushton, D. J.; Bos, M.; Verboom, W.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1992, 111, 415.
23. (q) Reichwein, A. M.; Verboom, W.; Reinhoudt D. N. Recl. Trav. Chim. Pays-Bas 1993, 112, 595.
24. (r) Qian, P.; Matsuda, M.; Miyashita, T. J. Am. Chem. Soc. 1993, 115, 5624.
25. Kranz, M.; Clark, T.; v. R. Schleyer, P. J. Org. Chem. 1993, 58, 3317. Carter, R. E.; Liljefors, T. Tetrahedron 1976, 32, 2915.
26. Kranz, M.; Clark, T.; v. R. Schleyer, P. J. Org. Chem. 1993, 58, 3317. Carter, R. E.; Liljefors, T. Tetrahedron 1976, 32, 2915.
27. In this context, P and M helicity refers to the (conformational) helicity along the biaryl axis irrespectively of the sequence rule of the substituent eventually present, as defined in Figure 1: see, for example: Testa, B. In Principles of Organic Stereochemistry; Dekker: New York, 1979; p 71.
28. Harada, T.; Takeuchi, M.; Hatsuda, M.; Ueda, S.; Oku, A. Tetrahedron Asymm. 1996, 7, 2479.
29. (a) Lustenberger, P.; Martinborough, E.; Mordasini Denti, T.; Diederich, F. J. Chem. Soc., Perkin Trans. 2 1998, 747.
30. (b) Lustenberger, P.; Welti, R.; Diederich, F. Helv. Chim. Acta 1998, 81, 2190.
31. The case of 1,1′-binaphthalene is remarkable to point out the role of the crystal packing in the determination of the actual conformation: in the enantiomerically pure form 1,1′-binaphthalene crystallizes in a s-trans conformation (θ = 103.1°) (Kuroda, R.; Mason, S. F. J. Chem. Soc., Perkin Trans. 2 1981, 167) while in the racemic composition as an s-cis rotamer (θ = 68.6°) (Kerr, K. A.; Robertson, J. M. Chem. Soc. B 1969, 1146). See also: Kress, R. B.; Duesler, E. N.; Etter, M. C.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1980, 102, 7709.
32. The case of 1,1′-binaphthalene is remarkable to point out the role of the crystal packing in the determination of the actual conformation: in the enantiomerically pure form 1,1′-binaphthalene crystallizes in a s-trans conformation (θ = 103.1°) (Kuroda, R.; Mason, S. F. J. Chem. Soc., Perkin Trans. 2 1981, 167) while in the racemic composition as an s-cis rotamer (θ = 68.6°) (Kerr, K. A.; Robertson, J. M. Chem. Soc. B 1969, 1146). See also: Kress, R. B.; Duesler, E. N.; Etter, M. C.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1980, 102, 7709.
33. The case of 1,1′-binaphthalene is remarkable to point out the role of the crystal packing in the determination of the actual conformation: in the enantiomerically pure form 1,1′-binaphthalene crystallizes in a s-trans conformation (θ = 103.1°) (Kuroda, R.; Mason, S. F. J. Chem. Soc., Perkin Trans. 2 1981, 167) while in the racemic composition as an s-cis rotamer (θ = 68.6°) (Kerr, K. A.; Robertson, J. M. Chem. Soc. B 1969, 1146). See also: Kress, R. B.; Duesler, E. N.; Etter, M. C.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1980, 102, 7709.
34. 2 derivatives, see, for example: Eliel, E. L.; Wilen, S. H. In Stereochemistry of Organic Compounds; John Wiley: New York, 1994; pp 1147-1148. Di Bari, L.; Pescitelli, G.; Pizzanelli, S.; Rosini, C.; Salvadori, P. In Proceedings of the 10th International Symposium on Chiral Discrimination; Vienna, 1998.
35. 2 derivatives, see, for example: Eliel, E. L.; Wilen, S. H. In Stereochemistry of Organic Compounds; John Wiley: New York, 1994; pp 1147-1148. Di Bari, L.; Pescitelli, G.; Pizzanelli, S.; Rosini, C.; Salvadori, P. In Proceedings of the 10th International Symposium on Chiral Discrimination; Vienna, 1998.
36. Harada, N.; Nakanishi, K. In Circular Dichroic Spectroscopy -Exciton Coupling in Organic Stereochemistry; Oxford University Press: Oxford, 1983.
37. Mason, S. F.; Seal, R. H.; Roberts, D. R. Tetrahedron 1974, 30, 1671.
38. Hanazaki, I.; Akimoto, H. J. Am. Chem. Soc. 1972, 94, 4102.
39. Rosini, C.; Rosati, I.; Spada, G. P. Chirality 1995, 7, 353.
40. Di Bari, L.; Pescitelli, G.; Salvadori, P. J. Am. Chem. Soc. 1999, 121, 7998.
41. A review of the applications of this technique in solving stereochemical problems is given in: Spada, G. P.; Proni, G. Enantiomer 1998, 3, 301.
42. An attempt to relate the two quantities for chiral biaryls has been discussed in: Gottarelli, G.; Osipov, M. A.; Spada, G. P. J. Phys. Chem. 1991, 95, 3879.
43. Gottarelli, G.; Hibert, M.; Samorì, B.; Solladié, G.; Spada, G. P.; Zimmermann, R. J. Am. Chem. Soc. 1983, 105, 7318.
44. Gottarelli, G.; Spada, G. P.; Bartsch, R.; Solladié, G.; Zimmermann, R. J. Org. Chem. 1986, 51, 589.
45. Suchod, B.; Renault, A.; Lajzerowicz, J.; Spada, G. P. J. Chem. Soc., Perkin Trans. 2 1992, 1839. Rosini, C.; Franzini, L.; Salvadori, P.; Spada, G. P. J. Org. Chem. 1992, 57, 6820.
46. Suchod, B.; Renault, A.; Lajzerowicz, J.; Spada, G. P. J. Chem. Soc., Perkin Trans. 2 1992, 1839. Rosini, C.; Franzini, L.; Salvadori, P.; Spada, G. P. J. Org. Chem. 1992, 57, 6820.
47. Deussen, H. J.; Shibaev, P. V.; Vinokur, R.; Bjornholm, T.; Schaumburg, K.; Bechgaard, K.; Shibaev, V. P. Liq. Cryst. 1996, 21, 327.
48. Ferrarini, A.; Nordio, P. L.; Shibaev, P. V.; Shibaev, V. P. Liq. Cryst. 1998, 24, 219.
49. Bandini, M.; Casolari, S.; Cozzi, P. G.; Proni, G.; Schmohel, E.; Spada, G. P.; Tagliavini, E.; Umani Ronchi, A. Eur. J. Org. Chem. 2000, 491.
50. Gottarelli, G.; Mariani, P.; Spada, G. P.; Samorì, B.; Forni, A.; Solladié, G.; Hibert, M. Tetrahedron 1983, 39, 1337. Gottarelli, G.; Spada, G. P.; Seno, K.; Hagishita, S.; Kuriyama, K. Bull. Chem. Soc. Jpn. 1986, 59, 1607. Arnone, C.; Gottarelli, G.; Spada, G. P.; Spinelli, D. J. Mol. Struct. 1986, 147, 307.
51. Gottarelli, G.; Mariani, P.; Spada, G. P.; Samorì, B.; Forni, A.; Solladié, G.; Hibert, M. Tetrahedron 1983, 39, 1337. Gottarelli, G.; Spada, G. P.; Seno, K.; Hagishita, S.; Kuriyama, K. Bull. Chem. Soc. Jpn. 1986, 59, 1607. Arnone, C.; Gottarelli, G.; Spada, G. P.; Spinelli, D. J. Mol. Struct. 1986, 147, 307.
52. Gottarelli, G.; Mariani, P.; Spada, G. P.; Samorì, B.; Forni, A.; Solladié, G.; Hibert, M. Tetrahedron 1983, 39, 1337. Gottarelli, G.; Spada, G. P.; Seno, K.; Hagishita, S.; Kuriyama, K. Bull. Chem. Soc. Jpn. 1986, 59, 1607. Arnone, C.; Gottarelli, G.; Spada, G. P.; Spinelli, D. J. Mol. Struct. 1986, 147, 307.
53. Gottarelli, G.; Proni, G.; Spada, G. P.; Fabbri, D.; Gladiali, S.; Rosini, C. J. Org. Chem. 1996, 61, 2013.
54. Ferrarini, A.; Moro, G. J.; Nordio, P. L. Mol. Phys. 1996, 87, 485. Ferrarini, A.; Moro, G. J.; Nordio, P. L. Phys. Rev. E 1996, 53, 681.
55. Ferrarini, A.; Moro, G. J.; Nordio, P. L. Mol. Phys. 1996, 87, 485. Ferrarini, A.; Moro, G. J.; Nordio, P. L. Phys. Rev. E 1996, 53, 681.
56. Chilaya, G.; Oestreicher, F.; Scherowsky, G. Mol. Materials 1998, 9, 261.
57. Ferrarini, A.; Gottarelli, G.; Nordio, P. L.; Spada, G. P. J. Chem. Soc., Perkin Trans. 2 1999, 411.
58. Green, M. M.; Zanella, S.; Gu, H.; Sato, T.; Gottarelli, G.; Jha, S. K.; Spada, G. P.; Schoevaars, J. M.; Feringa, B.; Teramoto, A. J. Am. Chem. Soc. 1998, 120, 9810.
59. Bauman, D.; Martynski, T.; Mykowska, E. Liq. Cryst. 1995, 18, 607.
60. Williams, V. E.; Lemieux, R. P. J. Am. Chem. Soc. 1998, 120, 11311.
61. Heppke, G.; Oestreicher; F. Z. Naturforsch., A 1977, 32a, 899.
62. Gottarelli, G.; Samorì, B.; Stremmenos, C.; Torre, G. Tetrahedron 1981, 37, 395. Berthault, J.-P. Thesis, Université de Paris, 1977.
63. Gottarelli, G.; Samorì, B.; Stremmenos, C.; Torre, G. Tetrahedron 1981, 37, 395. Berthault, J.-P. Thesis, Université de Paris, 1977.