A General Synthetic Route to 4-Substituted-2,2′-Bithiophenes

Journal of Heterocyclic Chemistry

Volumn 34, Issue 1, 1997, Pages 285-288

  Rasmussen, Seth C ^a   Pickens, Jason C ^a   Hutchison, James E ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003150845     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340143     Document Type: Article

References (34)

1. A. Carpita and R. Rossi, Gazz. Chim. Ital., 115, 575 (1985).
2. M. D'Auria, A. De Mico, F. D'Onofrio and G. Piancatelli, J. Org. Chem., 52, 5243 (1987).
3. M. D'Auria, A. De Mico, F. D'Onofrio and G. Piancatelli, J. Chem. Soc., Perkin Trans. I, 1777 (1987).
4. J. Roncali, Chem. Rev., 92, 711 (1992).
5. M. Zagórska and B. Krische, Polymer, 31, 1379 (1990).
6. K. Faïd, R. Cloutier and M. Ledere, Macromolecules, 26, 2501 (1993).
7. P. F. van Hutten, R. E. Gill, J. K. Herrema and G. Hadziioannou, J. Phys. Chem., 99, 3218 (1995).
8. M. R. Andersson, M. Berggren, O. Inganäs, G. Gustafsson, J. C. Gustafsson-Carlberg, D. Selse, T. Hjertberg and O. Wennerström, Macromolecules, 28, 7525 (1995).
9. M. R. Andersson, Q. Pei, T. Hjertberg, O. Inganäs, O. Wennerström and J.-E. Österholm, Synth. Met., 55-57, 1227 (1993).
10. H. Masuda, K. Kaeriyama, H. Suezawa and M. Hirota, J. Polym. Sci., Part A, Polym. Chem., 30, 945 (1992).
11. S. Gronowitz and A. Svensson, Isr. J. Chem., 27, 25 (1986).
12. N. Jayasuriya and J. Kagan, Heterocycles, 24, 2901 (1986).
13. T. Masquelin and D. Obrecht, Tet. Lett., 35, 9387 (1994).
14. F. Demanze, A. Yassar and F. Garnier, Adv. Mater., 7, 907 (1995).
15. E. Khor, S. Choon Ng, H. Chze Li and S. Chai, Heterocycles, 32, 1805 (1991).
16. E. Schulz, K. Fahmi and M. Lemaire, Acros Organics Acta, 1, 10 (1995).
17. S. Gronowitz, Arkiv Kemi, 8, 441 (1955).
18. 1H nmr; [b] S. Bien, M. Kapon, S. Gronowitz and A.-B. Hörnfeldt, Chem. Scripta, 29, 221 (1989); [c] G. T. Crisp, Synth. Commun., 19, 307 (1989).
19. 1H nmr; [b] S. Bien, M. Kapon, S. Gronowitz and A.-B. Hörnfeldt, Chem. Scripta, 29, 221 (1989); [c] G. T. Crisp, Synth. Commun., 19, 307 (1989).
20. 1H nmr; [b] S. Bien, M. Kapon, S. Gronowitz and A.-B. Hörnfeldt, Chem. Scripta, 29, 221 (1989); [c] G. T. Crisp, Synth. Commun., 19, 307 (1989).
21. P. Moses and S. Gronowitz, Arkiv Kemi, 18, 119 (1961).
22. S. Gronowitz, Adv. Heterocyclic Chem., 1, 1 (1963).
23. H. L. Lewis and T. L. Brown, J. Am. Chem. Soc., 92, 4664 (1970).
24. B. J. Wakefield, The Chemistry of Organolithium Compounds, Pergamon Press, New York, 1974, p 8.
25. F. A. Carey and R. J. Sundberg, Advanced Organic Chemistry, 3rd Ed, Part A: Structure and Mechanisms, Plenum Press, New York, 1990, p 405.
26. G. G. Eberhardt and W. A. Butte, J. Org. Chem., 29, 2928 (1964).
27. S. Gronowitz, Acta Chem. Scand., 15, 1393 (1961).
28. S. Gronowitz, Arkiv Kemi, 7, 267 (1954).
29. S. Gronowitz, Artiv Kemi, 12, 115 (1957).
30. D. E. Pearson, D. Cowan and J. D. Becker, J. Org. Chem., 24, 504 (1959).
31. F. A. Cotton and G. Wilkinson, Advanced Inorganic Chemistry, 5th Ed., John Wiley & Sons, New York, 1988, p 159.
32. M. Kumada, K. Tamao and K. Sumitani, Org. Synth., 58, 127 (1978).
33. K. Tamao, S. Kodama, I. Nakajima, M. Kumada, A. Minato and K. Suzuki, Tetrahedron, 38, 3347 (1982).
34. The reaction is sometimes very slow to initiate and some crushing of the magnesium may be required.