Synthesis of 3,4′-dibromo-2,2′-bithiophene: A useful intermediate for 3,4′-disubstituted 2,2′-bithiophenes. X-ray molecular structure of 3,4′-dibromo-2,2′-bithiophene

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 13, 1997, Pages 1957-1961

  Antolini, Luciano ^a   Goldoni, Francesca ^a   Iarossi, Dario ^a   Mucci, Adele ^a   Schenetti, Luisa ^a  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748729652     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700811b     Document Type: Article

References (52)

1. J. Roncali, Chem. Rev., 1992, 92, 711.
2. M. R. Andersson, M. Berggren, O. Inganäs, G. Gustafsson, J. C. Gustafsson-Carlberg, D. Selse, T. Hjertberg and O. Wennerström, Macromolecules, 1995, 28, 7525.
3. N. Noma, T. Tsuzuki and Y. Shirota, Adv. Mater., 1995, 7, 647.
4. G. Horowitz, F. Garnier, A. Yassar, R. Hajlaoui and F. Kouki, Adv Mater., 1996, 8, 52.
5. H. Higuchi, H. Koyama, H. Yokota and J. Ojima, Tetrahedron Lett., 1996, 37, 1617;
6. C. Branger, M. Lequan, R. M. Lequan, M. Barzoukas and A. Fort, J. Mater. Chem., 1996, 6, 555.
7. Z. Gao, K. S. Siow and H. S. O. Chan, Synth. Met., 1995, 75, 5.
8. R. Rossi, A. Carpita, M. Ciofalo and J. L. Houben, Gazz. Chim. Ital., 1990, 120, 793;
9. A. MacEachern, C. Soucy, L. C. Leitch, J. T. Arnason and P. Morand, Tetrahedron, 1988, 44, 2403.
10. P. Bäuerle, G. Götz, A. Synowczyk and J. Heinze, Liebigs Ann. Chem., 1996, 279.
11. L. L. Miller and Y. Yu, J. Org. Chem., 1995, 60, 6813.
12. P. Bäuerle, F. Pfau, H. Schlupp, F. Würthner, K.-U. Gaudi, M. Balparda Caro and P. Fischer, J. Chem. Soc., Perkin Trans. 2, 1993, 489.
13. G. Zotti, M. C. Gallazzi, G. Zerbi and S. V. Meille, Synth. Met., 1995, 73, 217;
14. F. Demanze, A. Yassar and F. Garnier, Synth Met., 1996, 76, 269;
15. P. Bäuerle, G. Gotz, U. Segelbacher, D. Huttenlocher and M. Mehring, Synth. Met., 1993, 55-57, 4768;
16. G. Horowitz, P. Delannoy, H. Bouchriha, F. Deloffre, J.-L. Fave, F. Garnier, R. Hajlaoui, M. Heyman, F. Kouki, P. Valat, V. Wintgens and A. Yassar, Adv. Mater., 1994, 6, 752.
17. P. Bäuerle, T. Fisher, B. Bidlingmeier, A. Stabel and J. P. Rabe, Angew. Chem., Int. Ed. Engl., 1995, 34, 303;
18. H. Higuchi, T. Nakayama, H. Koyama, J. Ojima, T. Wada and H. Sasabe, Bull. Chem. Soc. Jpn., 1995, 68, 2363;
19. J. M. Tour and R. Wu, Macromolecules, 1992, 25, 1901.
20. T.-A. Chen, X. Wu and R. D. Rieke, J. Am. Chem. Soc., 1995, 117, 233;
21. M. D. McClain, D. A. Whittington, D. J. Mitchell and M. D. Curtis, J. Am. Chem. Soc., 1995, 117, 3887;
22. R. D. McCullough, S. P. Williams, S. Tristam-Nagle, M. Jayaraman, P. C. Ewbank and L. Miller, Synth. Met., 1995, 69, 279;
23. Y. Miyazaki and T. Yamamoto, Synth. Met., 1994, 64, 69.
24. M. J. Marsella, P. J. Carroll and T. M. Swager, J. Am. Chem. Soc., 1994, 116, 9347.
25. C. Arbizzani, G. Barbarella, A. Bongini, M. Mastragostino and M. Zambianchi, Synth. Met., 1992, 52, 329.
26. U. Folli, D. Iarossi, M. Montorsi, A. Mucci and L. Schenetti, J. Chem. Soc., Perkin Trans. 1, 1995, 537.
27. K. Faïd, R. Cloutier and M. Leclerc, Macromolecules, 1993, 26, 2501.
28. U. Folli, F. Goldoni, D. Iarossi, A. Mucci and L. Schenetti, J. Chem. Res. (S), 1996, 69.
29. E. Khor, S. C. Ng, H. C. Li and S. Chai, Heterocycles, 1991, 32, 1805.
30. E. Schulz, K. Fahmi and M. Lemaire, Acros Organics Acta, 1995, 1, 10.
31. (a) S. Gronowitz, Y. Zhang and A.-B. Hörnfeldt, Acta Chem. Scand., 1992, 46, 654;
32. (b) M. J. Naujan, V. Kannappan and R. Z. Ganesan, Plys. Chem., 1981, 127, 13.
33. F. Sauter, H. Fröhlich and W. Kalt, Synthesis, 1989, 771.
34. H. Fröhlich and W. Kalt, J. Org. Chem., 1990, 55, 2993.
35. L. Brandsma and H. D. Verkruijsse, Preparative Polar Organometallic Chemistry, Springer-Verlag, Berlin, 1987, vol. 1, pp. 123 and 160.
36. E. Negishi, T. Takahashi and A. O. King, Org. Synth., 1988, 66, 67 and references therein.
37. J. K. Stille, Pure Appl. Chem., 1985, 57, 1771.
38. E. W. Colvin, Chem. Soc. Rev., 1978, 7, 15.
39. T. H. Chan and I. Fleming, Synthesis, 1979, 761.
40. D. Habich and F. Effenberger, Synthesis, 1979, 841.
41. G. Barbarella, M. Zambianchi, A. Bongini and L. Antolini, J. Org. Chem., 1996, 61, 4708.
42. G. Barbarella, M. Zambianchi, A. Bongini and L. Antolini, Adv. Mater., 1993, 5, 834.
43. S. Hotta and K. Waragai, Adv. Mater., 1993, 5, 896.
44. G. J. Pyrka, Q. Fernando, M. B. Inoue, M. Inoue and E. Velazquez, Acta Crystallogr., Sect. C, 1988, 44, 562.
45. L. Antolini, unpublished results.
46. W. Porzio, S. Destri, M. Mascherpa and S. Brükner, Acta Polym., 1993, 44, 266.
47. A. Bax, R. H. Griffey and B. L. Hawkins, J. Magn. Reson., 1983, 55, 301.
48. A. Bax and M. F. Summers, J. Am. Chem. Soc., 1986, 108, 2093.
49. F. W. Wehrli and T. Wirthlin, Interpretation of Carbon-13 NMR Spectra, Heyden, Bristol, 1978.
50. F. Goldoni, D. Iarossi, A. Mucci, L. Schenetti and M. Zambianchi, J. Mater. Chem., 1997, 7, 593.
51. G. M. Sheldrick, SHELXS86, Acta Crystallogr., Sect. A, 1990, 46, 467.
52. G. M. Sheldrick, SHELXL93: Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1993.