Synthesis of 3,4-bis[(methoxycarbonyl)methyl]thiophene and bis-, ter- and pentathiophenes with alternating 3,4-bis[(methoxycarbonyl)methyl]- substituted rings

Tetrahedron

Volumn 55, Issue 2, 1999, Pages 485-502

  Fazio, Alessia ^a   Gabriele, Bartolo ^a   Salerno, Giuseppe ^a   Destri, Silvia ^b  

^a UNIVERSITY OF CALABRIA   (Italy)

^b CNR   (Italy)

Author keywords

Carbonylation; Coupling reactions; Palladium; Thiopenes

Indexed keywords

3,4 BIS[(METHOXYCARBONYL)METHYL]THIOPHENE; POLYMER; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONDUCTOR; ELECTRONICS; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033534577     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01047-3     Document Type: Article

References (32)

1. Press, J. B. Pharmacologically active compounds and other thiophene derivatives. In: Gronowitz, S., ed. Thiophene and its Derivatives, Vol 44 part one. New York, John Wiley, 1985; pp. 353-436.
2. Roncali, J. Chem. Rev. 1992, 92, 711-738.
3. Andersson, M. R.; Berggren, M.; Inganäs, O.; Gustafsson, G.; Gustafsson-Carberg, J. C.; Selse, D.; Hjertberg, T.; Wennerström, O. Macromolecules 1995, 28, 7525-7529.
4. McCullough, R. D.; Williams, S. P. J. Am. Chem. Soc. 1993, 115, 11608-11609.
5. McCullough, R. D; Jayaraman, M. J. Chem. Soc., Chem. Commun. 1995, 135-140.
6. Bojornholm, T.; Greve, D. R.; Gusler, T.; Petersen, J. C.; Jayaraman, M.; McCullough, R. D. Adv. Materials 1996, 8, 920-924.
7. Chen, T. A.; Wu, X.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 233-244.
8. Bounan, M. M.; Meijer, E. W. Adv. Materials 1995, 7, 385-387.
9. Taylor, R. Electrophilic substitution of thiophene and its derivatives. In: Gronowitz, S., ed. Thiophene and its Derivatives, vol 44 part two. New York, John Wiley, 1986; pp. 1-118.
10. Cagniant, P.; Cagniant, D.; Paquer, D.; Kirsch, G. Alkylthiophenes and their reactions. In: Gronowitz, S., ed. Thiophene and its Derivatives, vol 44 part two. New York, John Wiley, 1986; pp 119-158.
11. Gronowitz, S. Preparation of thiophenes by ring-closure reactions and from other ring systems. In: Gronowitz, S., ed. Thiophene and its Derivatives, vol 44 part one. New York, John Wiley, 1985; pp 1-214.
12. a) Gabriele, B.; Costa, M.; Salerno, G.; Chiusoli, G. P. J. Chem. Soc., Chem. Commun. 1992, 1007-1008;
13. b) Gabriele, B.; Costa, M.; Salerno, G.; Chiusoli, G. P. J. Chem. Soc., Perkin Trans. 1 1994, 83-87;
14. c) Gabriele, B.; Costa, M.; Salerno, G.; Chiusoli, G. P. J. Chem. Soc., Chem. Commun. 1994, 1429-1430;
15. d) Bonardi, A.; Costa, M.; Gabriele, B.; Salerno, G.; Chiusoli G. P. Tetrahedron Lett. 1995, 36, 7495-7498;
16. e) Gabriele, B.; Salerno, G.; De Pascali, F.; Costa, M.; Chiusoli, G. P. J. Chem. Soc., Perkin Trans. 1 1997, 147-154;
17. f) Bacchi, A.; Chiusoli, G. P.; Costa, M.; Gabriele, B.; Righi, C.; Salerno, G. Chem. Commun. 1997, 1209-1210;
18. g) Gabriele, B.; Salerno, G.; De Pascali, F.; Tomasi Scianò, G.; Costa, M.; Chiusoli, G. P. Tetrahedron Lett. 1997, 38, 6877-6880;
19. h) Bacchi, A.; Chiusoli, G. P.; Costa, M.; Sani, C.; Gabriele, B.; Salerno, G. J. Organomet. Chem. 1998, 562, 35-43.
20. Chiusoli, G. P.; Costa, M.;. Pergreffi, P.; Reverberi, S.; Salerno, G. Gazz. Chim. Ital. 1985, 115, 691-696.
21. Costa, M.; De Souza Santos, L.; Chiusoli, G. P.; Gabriele, B.; Salerno, G. J. Mol. Catal. 1993, 78, 151-158.
22. Chiusoli, G. P.; Costa, M.; Reverberi, S. Synthesis 1989, 262-265.
23. Guindon, Y.; Frenette, R.; Fortin, R.; Rokach, J. J. Org. Chem. 1983, 48, 1357-59.
24. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
25. Mitsunobu, O. Synthesis 1981, 1-28.
26. Eberhard, J. F.; Oakes, B. D. U.S. Pat. 3,037,934 1962 (Chem. Abstr. 1962, 57, P6970a).
27. Gal, Y. S.; Choi, S. K. J. Polymer Science: Part C Polymer Letters 1988, 26, 115-121.
28. Feringa, B. L.; Hulst, R.; Rikers, R.; Brandsma, L. Synthesis 1988, 316-318.
29. Zhenam, B.; Waikin, C.; Luping, Y. Chem. Mater. 1993, 5, 2-3.
30. Midland, M. M. J. Org. Chem. 1975, 40, 2250-2252.
31. Volante, R. P. Tetrahedron Lett. 1981, 22, 3119-3122.
32. Gauthier, J. Y.; Bourdon, F.; Young, R. N. Tetrahedron Lett. 1986, 27, 15-18.