Synthesis and properties of bis(2,5-dimethylpyrrolo[3,4-d])tetrathiafulvalenes, a class of annelated tetrathiafulvalene derivatives with excellent electron donor properties

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 8117-8124

  Zong, Kyukwan ^a   Chen, Wha ^a   Cava, Michael P ^a   Rogers, Robin D ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; CRYSTALLOGRAPHY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029839876     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961282h     Document Type: Article

References (32)

1. For a recent review: (a) In Synthetic Metals, Proceedings of the International Conference on Synthetic Metals ICSM 1986; Shirakawa, H., Yamabe, T., Eds.; Kyoto, Japan, 1987; Vol 17-19. (b) Schukat, G.; Richter, A. M.; Fanghanel, E. Sulfur Reports 1987, 7, 177. (c) Garin, J. Adv. Heterocycl. Chem. 1995, 62, 249. (d) Williams, J. M.; Ferraro, J. R.; Thorn, R. J.; Carlson, D. D.; Geiser, U.; Wang, H. H.; Kini, A. M.; Whangboo, M.-H, Organic Superconductors (Including Fullerenes); Synthesis, Structure, Properties, and Theory; Grimes, R. N., Ed.; Prentice Hall: Englewood Cliffs, NJ, 1992.
2. For a recent review: (a) In Synthetic Metals, Proceedings of the International Conference on Synthetic Metals ICSM 1986; Shirakawa, H., Yamabe, T., Eds.; Kyoto, Japan, 1987; Vol 17-19. (b) Schukat, G.; Richter, A. M.; Fanghanel, E. Sulfur Reports 1987, 7, 177. (c) Garin, J. Adv. Heterocycl. Chem. 1995, 62, 249. (d) Williams, J. M.; Ferraro, J. R.; Thorn, R. J.; Carlson, D. D.; Geiser, U.; Wang, H. H.; Kini, A. M.; Whangboo, M.-H, Organic Superconductors (Including Fullerenes); Synthesis, Structure, Properties, and Theory; Grimes, R. N., Ed.; Prentice Hall: Englewood Cliffs, NJ, 1992.
3. For a recent review: (a) In Synthetic Metals, Proceedings of the International Conference on Synthetic Metals ICSM 1986; Shirakawa, H., Yamabe, T., Eds.; Kyoto, Japan, 1987; Vol 17-19. (b) Schukat, G.; Richter, A. M.; Fanghanel, E. Sulfur Reports 1987, 7, 177. (c) Garin, J. Adv. Heterocycl. Chem. 1995, 62, 249. (d) Williams, J. M.; Ferraro, J. R.; Thorn, R. J.; Carlson, D. D.; Geiser, U.; Wang, H. H.; Kini, A. M.; Whangboo, M.-H, Organic Superconductors (Including Fullerenes); Synthesis, Structure, Properties, and Theory; Grimes, R. N., Ed.; Prentice Hall: Englewood Cliffs, NJ, 1992.
4. For a recent review: (a) In Synthetic Metals, Proceedings of the International Conference on Synthetic Metals ICSM 1986; Shirakawa, H., Yamabe, T., Eds.; Kyoto, Japan, 1987; Vol 17-19. (b) Schukat, G.; Richter, A. M.; Fanghanel, E. Sulfur Reports 1987, 7, 177. (c) Garin, J. Adv. Heterocycl. Chem. 1995, 62, 249. (d) Williams, J. M.; Ferraro, J. R.; Thorn, R. J.; Carlson, D. D.; Geiser, U.; Wang, H. H.; Kini, A. M.; Whangboo, M.-H, Organic Superconductors (Including Fullerenes); Synthesis, Structure, Properties, and Theory; Grimes, R. N., Ed.; Prentice Hall: Englewood Cliffs, NJ, 1992.
5. Urama, H.; Yamochi, H.; Saito, G.; Nozawa, K.; Sugano, T.; Kinoshita, M.; Sato, S.; Oshima, K.; Kawamoto, A.; Tanaka, J. Chem. Lett. 1988, 55.
6. Lerstrup, K.; Talham, D.; Bloch, A.; Cowan, D. J. Chem. Soc., Chem. Commun. 1982, 336.
7. Shu, P.; Chiang, L.; Emge, T.; Holt, D.; Kistenmacher, T.; Lee, M.; Stokes, J.; Poehler, T.; Cowan, D. J. Chem. Soc., Chem. Commun. 1981, 920.
8. Cowan, D. O; Chiang, L.-Y.; Shu, P.; Holt, D. J. Org. Chem. 1983, 48, 473.
9. Ketchwan, R.; Hornfeldt, A.-B.; Gronowitz, S. J. Org. Chem. 1984, 49, 1117.
10. Chen, W.; Cava, M. P.; Takassi, M. A.; Metzger, R. M. J. Am. Chem. Soc. 1988, 110, 7903.
11. Matteson, D. S.; Snyder, H. R. J. Am. Chem. Soc. 1857, 79, 3610.
12. Soderback, K.; Gronowitz, S. Acta. Chem. Scand. 1961, 15, 227.
13. Ueno, Y.; Nozomi, M.; Okawara, M. Chem. Lett. 1982, 1119.
14. (a) The Chemistry of the Thiol Group; Patai, S., Ed.; Chemistry of Functional Groups 31; John Wiley & Sons: London, 1974.
15. (b) Schoberl, A.; Wagner, A. Methoden Der Organischen Chemie; Georg Thieme Verlag: Stuttgart, 1955; Chapter IX, p 23.
16. (c) Ookawa, A.; Yokoyama, S.; Soai, K. Synth. Commun. 1986, 22, 1500.
17. Maiti, S. N.; Spevak, P.; Singh, M. P.; Reddy, N. Synth. Commun. 1988, 18, 575.
18. Tarbell, D. S.; Harnish, D. P. Chem. Rev. 1951, 49, 79.
19. Rawal, V. H.; Cava, M. P. Tetrahedron Lett. 1985, 26, 6141.
20. Al-awar, R.; Wahl, G. H., Jr. J. Chem. Educ. 1990, 67, 265.
21. Parg, P. R.; Kilburn, J. D.; Ryan, T. G. Synthesis 1994, 195.
22. (a) Klingsberg, E. J. Am. Chem. Soc. 1962, 84, 3410.
23. (b) Ibid. 1964, 86, 5290.
24. Coflfen, D. L.; Chambers, J. Q.; Williams, D. R.; Garrett, P. E.; Canfield, N. D. J. Am. Chem. Soc. 1971, 93, 2258.
25. (a) Rondestvedt, C. Org. React. 1976, 24, 225.
26. (b) Ibid. 1960, 11, 198.
27. Hurtly, W. R. H.; Smiles, S. J. Chem. Soc. 1926, 2263.
28. Bajwa, G. S.; Berlin, K. D.; Pohl, H. A. J. Org. Chem. 1976, 41, 145.
29. Mizuno, M.; Cava, M. P. J. Org. Chem. 1978, 43, 416.
30. Ueno, Y.; Nakayama, A.; Okawara, M. J. Am. Chem. Soc. 1976, 98, 7440.
31. Svenstrup, N.; Rasmussen, K. M.; Hansen, T. K.; Becher, J. Sythesis 1994, 809.
32. Wudl, F.; Bryce, M. R. J. Chem. Educ. 1990, 67, 717.