Induction of cholesteric mesophases by simple cyclic derivatives of p,p'-disubstituted 1,2-diphenylethane-1,2-diols: Importance of shape and polarizability effects

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4762-4767

  Superchi, Stefano ^a   Donnoli, Maria Irene ^a   Proni, Gloria ^b   Spada, Gian Piero ^b   Rosini, Carlo ^a  

^a UNIVERSITY OF BASILICATA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIDENE DERIVATIVE; BIPHENYL DERIVATIVE; ETHANE;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; ELECTRICITY; MOLECULAR DYNAMICS; NONHUMAN; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033603524     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990038y     Document Type: Article

References (50)

1. (a) A general introduction to liquid crystals, including chiral mesophases, can be found in: Collings, P. J.; Hird, M. Introduction to liquid crystals - Chemistry and Physics; Taylor & Francis: London, 1997.
2. (b) A more specific treatment of cholesteric systems is given by: Solladiè, G.; Zimmermann, R. G. Angew. Chem., Int. Ed. Engl. 1984, 23, 348.
3. Examples of stereochemical applications are reported in: (a) Gottarelli, G.; Spada, G. P.; Solladiè, G. Nouv. J. Chem. 1986, 10, 692. (b) Gottarelli, G.; Spada, G. P. Mol. Cryst. Liq. Cryst. 1985, 123, 37. (c) Spada, G. P.; Proni, G. Enantiomer 1998, 3, 301.
4. Examples of stereochemical applications are reported in: (a) Gottarelli, G.; Spada, G. P.; Solladiè, G. Nouv. J. Chem. 1986, 10, 692. (b) Gottarelli, G.; Spada, G. P. Mol. Cryst. Liq. Cryst. 1985, 123, 37. (c) Spada, G. P.; Proni, G. Enantiomer 1998, 3, 301.
5. Examples of stereochemical applications are reported in: (a) Gottarelli, G.; Spada, G. P.; Solladiè, G. Nouv. J. Chem. 1986, 10, 692. (b) Gottarelli, G.; Spada, G. P. Mol. Cryst. Liq. Cryst. 1985, 123, 37. (c) Spada, G. P.; Proni, G. Enantiomer 1998, 3, 301.
6. See, for instance: Scheuble, B. S. Kontakte 1989, 1, 34. Liquid Crystals. Applications and Uses; Bahadur, B., Ed.; World Scientific: Singapore, 1990 (Vol. 1); 1991 (Vol. 2); 1993 (Vol. 3).
7. See, for instance: Scheuble, B. S. Kontakte 1989, 1, 34. Liquid Crystals. Applications and Uses; Bahadur, B., Ed.; World Scientific: Singapore, 1990 (Vol. 1); 1991 (Vol. 2); 1993 (Vol. 3).
8. See, for instance: Scheuble, B. S. Kontakte 1989, 1, 34. Liquid Crystals. Applications and Uses; Bahadur, B., Ed.; World Scientific: Singapore, 1990 (Vol. 1); 1991 (Vol. 2); 1993 (Vol. 3).
9. See, for instance: Scheuble, B. S. Kontakte 1989, 1, 34. Liquid Crystals. Applications and Uses; Bahadur, B., Ed.; World Scientific: Singapore, 1990 (Vol. 1); 1991 (Vol. 2); 1993 (Vol. 3).
10. Highly efficient inducere have been recently described in: Park, J. J.; Sternhell, S.; Vonwiller, S. C. J. Org. Chem. 1998, 63, 6749. Kuball, H.-G.; Weiss, B.; Beck, A. K.; Seebach, D. Helv. Chim. Acta 1997,80,2507. Deussen, H.-J.; Shibaev, P. V.; Vinokur, R.; Bjornholm, T.; Schaumburg, K.; Bechgaard, K.; Shibaev, V. P. Liq. Cryst. 1996, 21, 327.
11. Highly efficient inducere have been recently described in: Park, J. J.; Sternhell, S.; Vonwiller, S. C. J. Org. Chem. 1998, 63, 6749. Kuball, H.-G.; Weiss, B.; Beck, A. K.; Seebach, D. Helv. Chim. Acta 1997,80,2507. Deussen, H.-J.; Shibaev, P. V.; Vinokur, R.; Bjornholm, T.; Schaumburg, K.; Bechgaard, K.; Shibaev, V. P. Liq. Cryst. 1996, 21, 327.
12. Highly efficient inducere have been recently described in: Park, J. J.; Sternhell, S.; Vonwiller, S. C. J. Org. Chem. 1998, 63, 6749. Kuball, H.-G.; Weiss, B.; Beck, A. K.; Seebach, D. Helv. Chim. Acta 1997,80,2507. Deussen, H.-J.; Shibaev, P. V.; Vinokur, R.; Bjornholm, T.; Schaumburg, K.; Bechgaard, K.; Shibaev, V. P. Liq. Cryst. 1996, 21, 327.
13. Williams, V. E.; Lemieux, R. P. J. Chem. Soc., Chem. Commun. 1996, 2259.
14. (a) Hunter, C. A. Angew. Chem., Int. Ed. Engl., 1993, 32, 1585.
15. (b) Hunter, C. A. Chem. Soc. Rev. 1994, 101.
16. (c) Hunter, C. A.; Saunders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
17. (d) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1996, 67, 683.
18. (e) Shetty, A S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019.
19. (f) Williams, V. E.; Lemieux, R. P.; Thatcher, G. R. J. J. Org. Chem. 1996, 61, 1927.
20. (g) García Martínez, A.; Osío Barcina, J.; de Fresno Cerezo, A.; Gutiérrez Rivas, R. J. Am Chem. Soc. 1998, 120, 673.
21. Dougherty, D. A. Science 1996, 271, 163. Ngola, S. M.; Dougherty, D. A. J. Org. Chem. 1998, 63, 4566.
22. Dougherty, D. A. Science 1996, 271, 163. Ngola, S. M.; Dougherty, D. A. J. Org. Chem. 1998, 63, 4566.
23. The importance of π-π interactions in asymmetric synthesis has been recently pointed out: Jones, G. B.; Chapman, B. J. Synthesis 1995, 475.
24. Tamaki, R.; Samura, K.; Chujo, Y. J. Chem. Soc., Chem. Commun. 1998, 1131.
25. Rosini, C.; Spada, G. P.; Proni, G.; Masiero, S.; Scamuzzi, S. J. Am. Chem. Soc. 1997, 119, 506.
26. Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
27. McMurry, J. E. Chem. Rev. 1989, 89, 1523.
28. Rosini, C.; Scamuzzi, S.; Pisani Focati, M.; Salvadori, P. J. Org. Chem. 1995, 60, 8289. Rosini, C.; Scamuzzi, S.; Uccello-Barretta, G.; Salvadori, P. J. Org. Chem. 1994, 59, 7395.
29. Rosini, C.; Scamuzzi, S.; Pisani Focati, M.; Salvadori, P. J. Org. Chem. 1995, 60, 8289. Rosini, C.; Scamuzzi, S.; Uccello-Barretta, G.; Salvadori, P. J. Org. Chem. 1994, 59, 7395.
30. Machinaga, N.; Kibayashi, H. Tetrahedron Lett. 1989, 31, 4165.
31. Lohray, B. B. Synthesis 1992, 1035.
32. Burk, R. M.; Roof, M. B. Tetrahedron Lett. 1993, 34, 395.
33. (a) Heppke, G.; Oestreicher, F. Z. Naturforsch. 1977, A32, 899.
34. (b) Heppke, G.; Oestreicher, F. Mol. Cryst. Liq. Cryst. 1978, 41, 245.
35. (c) Gottarelli, G.; Samorì, B.; Stremmenos, C.; Torre, G. Tetrahedron 1981, 37, 395.
36. MMX, Serena Software, P.O. Box 3076, Bloomington, IN 47402.
37. Gottarelli, G.; Mariani, P.; Spada, G. P.; Samorì, B.; Forni, A.; Solladié, G.; Hibert, M. Tetrahedron 1983, 39, 1337.
38. th ed.; Wiley-Interscience: New York, 1992; p 280.
39. Hansch, C.; Leo, A. J. Substituent Constants for Correlation Analysis in Chemistry and Biology; Wiley: New York, 1979.
40. Charton, M.; Ziffer, H. J. Org. Chem. 1987, 52, 2400.
41. Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99.
42. Gottarelli, G.; Hibert, M.; Samorì, B.; Solladié, G.; Spada, G. P.; Zimmermann, R. J. Am. Chem. Soc. 1983, 105, 7318.
43. For a description of the general theories of the molecular ordering in liquid crystal phases, see, for example: Madhusudana, N. V. In Liquid Crystals - Applications and Uses; Bahadur, B., Ed.; World Scientific: Singapore, 1990; Vol. 1, Chapter 2.
44. After the submission of this manuscript, we became aware of the following paper dealing with the role of dispersion and electrostatic forces on solute/solvent interactions in a nematic liquid crystal phase: Williams, V. E.; Lemieux, R. P. J. Am. Chem. Soc. 1998, 120, 11311.
45. Interestingly, theoretical models of cholesteric induction have been formulated only taking into account molecular shape factors: Ferrarini, A.; Moro, G. J.; Nordio, P. L. Phys. Rev. E 1996, 53, 681. Memmer, R.; Kuball, H. G.; Schönhofer, A. Mol. Phys. 1996, 89, 1633.
46. Interestingly, theoretical models of cholesteric induction have been formulated only taking into account molecular shape factors: Ferrarini, A.; Moro, G. J.; Nordio, P. L. Phys. Rev. E 1996, 53, 681. Memmer, R.; Kuball, H. G.; Schönhofer, A. Mol. Phys. 1996, 89, 1633.
47. Murthy, K. S. K.; Dhar, D. N. J. Heterocycl. Chem. 1984, 21, 1721.
48. (a) Iida, T.; Itaya, T. Tetrahedron 1993, 49, 10511.
49. (b) Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409.
50. Nymann, K.; Svendsen, J. S. Acta Chem. Scand. 1994, 48, 183.