General, efficient route to thiophene-1-oxides and well-defined, mixed thiophene-thiophene-1-oxide oligomers [12]

Journal of the American Chemical Society

Volumn 121, Issue 41, 1999, Pages 9744-9745

  Jiang, Biwang ^a   Tilley, T Don ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOMER; POLYMER; SULFUR DIOXIDE; THIOPHENE 1 OXIDE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG; ZIRCONIUM DERIVATIVE;

DEUTERON NUCLEAR MAGNETIC RESONANCE; INFRARED SPECTROSCOPY; LETTER; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032731885     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992365t     Document Type: Letter

References (33)

1. (a) Treiber, A.; Dansette, P. M.; El Amri, H.; Girault, J. P.; Ginderow, D.; Mornon, J. P.; Nasuy, D. J. Am. Chem. Soc. 1997, 119, 1565.
2. (b) Lopez-Garcia, M. P.; Dansette, P. M.; Mansuy, D. Biochemsitry 1994, 33, 166.
3. (a) Mock, W. L. J. Am. Chem. Soc. 1970, 92, 7610.
4. (b) Li, Y.; Matsuda, M.; Thiemann, T.; Sawada, T.; Mataka, S.; Tashiro, M. Synlett 1996, 461.
5. (c) Furukawa, N.; Zhang, S.; Sato, S.; Higaki, M. Heterocycles 1997, 44, 61.
6. (d) Pouzet, P.; Erdelmeier, I.; Ginderow, D.; Mornon, J.-P.; Dansette, P., Mansuy, D. J. Chem. Soc., Chem. Commun. 1995, 473.
7. (e) Nakayama, J.; Yu, T.; Sugihara, Y.; Ishii, A. Chem. Lett. 1997, 499.
8. (f) Hashmall, J. A.; Horak, V.; Khoo, L. E.; Quicksall, C. O.; Sun, M. K. J. Am. Chem. Soc. 1981, 103, 289.
9. (g) Skaugset, A. E.; Rauchfuss, T. B.; Stern, C. L. J. Am. Chem. Soc. 1990, 112, 2432.
10. Reviews: (a) Nakayama, J.; Sugihara Y. Sulfur Rep. 1997, 19, 349. (b) Kellog, R. M. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, U.K., 1984; Vol 4, p 713. (c) Raasch, M. S. In Chemistry of Heterocyclic Compounds, Thiophene and its Derivatives; Gronowitz, S., Ed.; Wiley: New York, 1985; Vol 44, p 971.
11. Reviews: (a) Nakayama, J.; Sugihara Y. Sulfur Rep. 1997, 19, 349. (b) Kellog, R. M. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, U.K., 1984; Vol 4, p 713. (c) Raasch, M. S. In Chemistry of Heterocyclic Compounds, Thiophene and its Derivatives; Gronowitz, S., Ed.; Wiley: New York, 1985; Vol 44, p 971.
12. Reviews: (a) Nakayama, J.; Sugihara Y. Sulfur Rep. 1997, 19, 349. (b) Kellog, R. M. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, U.K., 1984; Vol 4, p 713. (c) Raasch, M. S. In Chemistry of Heterocyclic Compounds, Thiophene and its Derivatives; Gronowitz, S., Ed.; Wiley: New York, 1985; Vol 44, p 971.
13. (a) Fagan, P. J.; Nugent, W. A. J. Am. Chem. Soc. 1988, 110, 2310.
14. (b) Fagan, P. J.; Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1994, 116, 1880.
15. (c) Meier-Brocks, F.; Weiss, E. J. Organomet. Chem. 1993, 33, 453.
16. (a) Mao, S. S. H.; Tilley, T. D. J. Organomet. Chem. 1996, 521, 425.
17. (b) Mao, S. S. H.; Tilley, T. D. Macromolecules 1997, 30, 5566.
18. (c) Lucht, B. L.; Tilley, T. D. Chem. Commun. 1998, 1645.
19. (d) Lucht, B. L.; Mao, S. S. H.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 4354.
20. (a) Lucht, B. L.; Buretea, M. A.; Tilley, T. D., manuscript in preparation.
21. (b) Jiang, B.; Tilley, T. D., unpublished results.
22. (a) Barbarella, G.; Favaretto, L.; Zambianchi, M.; Pudova, O.; Arbizzani, C.; Bongini, A.; Mastragostino, M. Adv. Mater. 1998, 10, 551.
23. (b) Barbarella, G.; Pudova, O.; Arbizzani, C.; Mastragostino, M.; Bongini, A. J. Org. Chem. 1998, 63, 1742.
24. (c) Barbarella, G.; Favaretto, L.; Zambianchi, M.; Antolini, L.; Pudova, O.; Bongini, A. J. Org. Chem. 1998, 63, 5497.
25. (a) Tanaka, K.; Wang, S.; Yamabe, T. Synth. Met. 1989, 30, 57.
26. (b) Bakhshi, A. K. Solid State Commun. 1995, 94, 943.
27. (a) Schlüler, A.-D. In Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1997; p 209.
28. (b) Yamamoto, T. Bull. Chem. Soc. Jpn. 1999, 72, 621.
29. (a) Negishi, E.; Cederbaum; F. E.; Takahashi; T. Tetrahedron Lett. 1986, 27, 2829.
30. (b) Negishi, E.; Takahashi; T. Acc. Chem. Res. 1994, 27, 124.
31. Furukawa, N.; Zhang, S.-Z.; Horn, E.; Takahashi, O.; Sato, S.; Yokoyama, M.; Yamaguchi, K. Heterocycles 1998, 47, 793.
32. The lower yield for 2f results from some debromination during its synthesis.
33. Yamaguchi, S.; Itami, Y.; Tamao, K. Organometallics 1998, 17, 4910.