Collect. Czech. Chem. Commun.
2003, 68, 1020-1038
https://doi.org/10.1135/cccc20031020
Axially Chiral 3,3'-Bi(1-benzothiophene)-2,2'-dicarboxylic Acid and Its Derivatives
Marie Mézlováa, Hana Petříčkováb, Petr Maloňc, Václav Kozmíka and Jiří Svobodaa,*
a Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, CZ-166 28 Prague 6, Czech Republic
b Department of Solid State Chemistry, Institute of Chemical Technology, Prague, Technická 5, CZ-166 28 Prague 6, Czech Republic
c Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, CZ-160 10 Prague 6, Czech Republic
References
1. Demus D., Goodby J., Gray G. W., Spiess H.-W., Vill V. (Eds): Handbook of Liquid Crystals. Wiley-VCH, Weinheim 1998.
2. Lagerwall S. T.: Ferroelectric and Antiferroelectric Liquid Crystals. Wiley-VCH Verlag, Weinheim 1999.
3. H.-D., Gopfert A.: Colloid Polym. Sci. 2000, 278, 1085.
4. R., Zab K., Tschierke C.: J. Prakt. Chem. 1998, 340, 662.
<https://doi.org/10.1002/prac.19983400711>
5. R., Tschierke C., Langhoff A., Giesselmann F., Zugenmaier P.: J. Mater. Chem. 1997, 7, 1713.
<https://doi.org/10.1039/a701032j>
6. Y., Schuster G. B.: J. Org. Chem. 1994, 59, 1855.
<https://doi.org/10.1021/jo00086a042>
7. R. P., Schuster G. B.: J. Org. Chem. 1993, 58, 100.
<https://doi.org/10.1021/jo00053a021>
8. G., Zimmermann R.: J. Org. Chem. 1985, 50, 4062.
<https://doi.org/10.1021/jo00221a020>
9. G., Hugelé P., Bartsch R., Skoulios A.: Angew. Chem., Int. Ed. Engl. 1996, 35, 1533.
<https://doi.org/10.1002/anie.199615331>
10. G., Hugele P., Bartsch R.: J. Org. Chem. 1998, 63, 3895.
<https://doi.org/10.1021/jo972143i>
11. P., Svoboda J., Glogarová M., Stibor I.: Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A 1999, 328, 367.
<https://doi.org/10.1080/10587259908026079>
12. K., Svoboda J., Stibor I., Glogarová M., Vaněk P., Novotná V.: Ferroelectrics 2000, 241, 248.
<https://doi.org/10.1080/00150190008224996>
13. Košata B., Kozmík V., Svoboda J., Novotná V., Vaněk P., Glogarová M.: Liq. Cryst. 2003, 30, in press.
14. Helmchen G., Hoffmann R. W., Mulzer J., Schaumann E. (Eds): Houben–Weyl: Methods of Organic Chemistry, Bd. E21a, Stereoselective Synthesis. G. Thieme Verlag, Stuttgart 1995.
15. R., Takaya H.: Acc. Chem. Res. 1990, 23, 345.
<https://doi.org/10.1021/ar00178a005>
16. T., Brenna E., Sannicolo F., Trimarco L., Antognazza P., Cesarotti E., Demartin F., Pilati T.: J. Org. Chem. 1996, 61, 6244.
<https://doi.org/10.1021/jo960211f>
17. T., Piccolo O., Rizzo S., Sannicolo F.: J. Org. Chem. 2000, 65, 8340.
<https://doi.org/10.1021/jo001207d>
18. M., Havelková M., Terinek M., Paleček J., Svoboda J., Jandera A., Panajotová V., Kuchař M.: Cesk. Farm. 1999, 48, 281.
19. J., Štádler M., Jandera A., Panajotová V., Kuchař M.: Collect. Czech. Chem. Commun. 2000, 65, 1082.
<https://doi.org/10.1135/cccc20001082>
20. N., Suzuki A.: Chem. Rev. (Washington, D. C.) 1995, 95, 2457.
<https://doi.org/10.1021/cr00039a007>
21. E.: Acc. Chem. Res. 1982, 15, 340.
<https://doi.org/10.1021/ar00083a001>
22. V.: Pure Appl. Chem. 1996, 68, 73.
<https://doi.org/10.1351/pac199668010073>
23. P. E.: Synthesis 1974, 9.
<https://doi.org/10.1055/s-1974-23219>
24. T. D., Meyers A. I.: J. Org. Chem. 1994, 59, 2655.
<https://doi.org/10.1021/jo00088a066>
25. A. I., McKennon M. J.: Tetrahedron Lett. 1995, 36, 5869.
<https://doi.org/10.1016/0040-4039(95)01180-P>
26. A. I., Price A.: J. Org. Chem. 1998, 63, 412.
<https://doi.org/10.1021/jo971761w>
27. T., Krubsack A. J.: J. Org. Chem. 1976, 41, 3399.
<https://doi.org/10.1021/jo00883a014>
28. W. B., Brabander H. J.: J. Heterocycl. Chem. 1971, 8, 711.
<https://doi.org/10.1002/jhet.5570080504>
29. W., Oremek G., Ocakcioglu B.: Justus Liebigs Ann. Chem. 1980, 1424.
<https://doi.org/10.1002/jlac.198019800911>
30. I., Kelsey D. R.: J. Org. Chem. 1986, 51, 2627.
<https://doi.org/10.1021/jo00364a002>
31. G., Hong R.: J. Org. Chem. 2001, 66, 2877.
<https://doi.org/10.1021/jo001563w>
32. H. D.: Acta Crystallogr., Sect. A: Fundam. Crystallogr. 1983, 39, 876.
<https://doi.org/10.1107/S0108767383001762>
33. L. J.: J. Appl. Crystallogr. 1997, 30, 565.
<https://doi.org/10.1107/S0021889897003117>
34. Nardelli M.: PARST, System of Computer Routines for Calculating Molecular Parameters from Results of Crystal Structure Analysis. University of Parma, Parma 1998.
35. S., Zhang D., Liebeskind L. S.: J. Org. Chem. 1997, 62, 2312.
<https://doi.org/10.1021/jo9700078>
36. H., Ohta T., Mashima K., Noyori R.: Pure Appl. Chem. 1990, 62, 1135.
<https://doi.org/10.1351/pac199062061135>
37. J. M.: Chem. Soc. Rev. 1993, 22, 25.
<https://doi.org/10.1039/cs9932200025>
38. R.: Pure Appl. Chem. 1981, 53, 2315.
<https://doi.org/10.1351/pac198153122315>
39. R., Tomino I., Tamimoto Y., Nishizawa M.: J. Am. Chem. Soc. 1984, 106, 6709.
<https://doi.org/10.1021/ja00334a041>
40. I., Zborovskii Y. L.: Zh. Org. Khim. 1975, 11, 1776.
41. W., Bender H.: Chem. Ber. 1955, 88, 34.
<https://doi.org/10.1002/cber.19550880107>
42. M. G., Newsom J. G., Almqvist K. A.: Synthesis 1980, 327.
<https://doi.org/10.1055/s-1980-29015>
43. Y., Pratap R., Castle R. N., Lee M. L.: J. Heterocycl. Chem. 1982, 19, 871.
<https://doi.org/10.1002/jhet.5570190432>
44. T., Krubsack A. J.: J. Org.Chem. 1975, 40, 3037.
<https://doi.org/10.1021/jo00909a007>
45. J., Scrowston R. M.: J. Chem. Soc., Perkin Trans. 1 1972, 414.
<https://doi.org/10.1039/p19720000414>
46. International Tables for Crystallography. D. Riedel Publishing Company, Boston 1983.
47. A., Cascarano G., Giacovazzo G., Guagliardi A., Burla M. C., Polidori G., Camalli M.: J. Appl. Crystallogr. 1994, 27, 435.
48. Watkin D. J., Prout C. K., Carruthers J. R., Betteridge P. W., Cooper R. I.: Crystals, p. 11. Chemical Crystallography Laboratory, Oxford (U.K.) 2001.
49. A. I., Dickman D. A., Bailey T. R.: J. Am. Chem. Soc. 1985, 107, 7974.
<https://doi.org/10.1021/ja00312a029>

