Syntheses, Unique Strained Molecular Structures, and Unusual Transannular Electronic Interactions of a Series of Crisscross-Overlapped Tetrathiafulvalenophanes

Journal of Organic Chemistry

Volumn 62, Issue 16, 1997, Pages 5567-5574

  Takimiya, Kazuo ^a   Imamura, Koichi ^a   Shibata, Youji ^a   Aso, Yoshio ^a   Ogura, Fumio ^a,b   Otsubo, Tetsuo ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b KINKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000358889     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962239x     Document Type: Article

References (25)

1. For a recent comprehensive review on dimeric TTFs, see: Otsubo, T.; Aso, Y.; Takimiya, K. Adv. Mater. 1996, 8, 203.
2. Kaplan, M. L.; Haddon, R. C.; Wudl, F. J. Chem. Soc., Chem. Commun. 1977, 388. Bechgaard, K.; Lerstrup, K.; Jørgensen, M.; Johannsen, I.; Christensen, J.; Larsen, J. Mol. Cryst. Liq. Cryst. 1990, 181, 161. Izuoka, A.; Kumai, R.; Tachikawa, T.; Sugawara, T. Ibid. 1992, 218, 213.
3. Kaplan, M. L.; Haddon, R. C.; Wudl, F. J. Chem. Soc., Chem. Commun. 1977, 388. Bechgaard, K.; Lerstrup, K.; Jørgensen, M.; Johannsen, I.; Christensen, J.; Larsen, J. Mol. Cryst. Liq. Cryst. 1990, 181, 161. Izuoka, A.; Kumai, R.; Tachikawa, T.; Sugawara, T. Ibid. 1992, 218, 213.
4. Kaplan, M. L.; Haddon, R. C.; Wudl, F. J. Chem. Soc., Chem. Commun. 1977, 388. Bechgaard, K.; Lerstrup, K.; Jørgensen, M.; Johannsen, I.; Christensen, J.; Larsen, J. Mol. Cryst. Liq. Cryst. 1990, 181, 161. Izuoka, A.; Kumai, R.; Tachikawa, T.; Sugawara, T. Ibid. 1992, 218, 213.
5. Ippen, J.; Tao-pen, C.; Starker, B.; Schweitzer, D.; Staab, H. A. Angew. Chem., Int. Ed. Engl. 1980, 19, 67. Bertho-Thoraval, F.; Robert, A.; Souizi, A.; Boubekeur, K.; Batail, P. J. Chem. Soc., Chem. Commun. 1991, 843; Adam, M.; Enkelmann, V.; Räder, H.-J.; Röhrich, J.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 309.
6. Ippen, J.; Tao-pen, C.; Starker, B.; Schweitzer, D.; Staab, H. A. Angew. Chem., Int. Ed. Engl. 1980, 19, 67. Bertho-Thoraval, F.; Robert, A.; Souizi, A.; Boubekeur, K.; Batail, P. J. Chem. Soc., Chem. Commun. 1991, 843; Adam, M.; Enkelmann, V.; Räder, H.-J.; Röhrich, J.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 309.
7. Ippen, J.; Tao-pen, C.; Starker, B.; Schweitzer, D.; Staab, H. A. Angew. Chem., Int. Ed. Engl. 1980, 19, 67. Bertho-Thoraval, F.; Robert, A.; Souizi, A.; Boubekeur, K.; Batail, P. J. Chem. Soc., Chem. Commun. 1991, 843; Adam, M.; Enkelmann, V.; Räder, H.-J.; Röhrich, J.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 309.
8. Takimiya, K.; Aso, Y.; Ogura, F.; Otsubo, T. Chem. Lett. 1995, 735.
9. Matsuo, K.; Takimiya, K.; Aso, Y.; Ogura, F.; Otsubo, T. Chem. Lett. 1995, 523.
10. Ferraro, J. R.; Williams, J. M. Introduction to Synthetic Electrical Conductors; Academic: San Diego 1987. Williams, J. M.; Ferraro, J. R.; Thorn, R. J.; Carlson, K. D.; Geiser, U.; Wang, H. H.; Kini, A. M.; Whangbo, M.-H. Organic Superconductors; Prentice-Hall: New Jersey, 1992.
11. Ferraro, J. R.; Williams, J. M. Introduction to Synthetic Electrical Conductors; Academic: San Diego 1987. Williams, J. M.; Ferraro, J. R.; Thorn, R. J.; Carlson, K. D.; Geiser, U.; Wang, H. H.; Kini, A. M.; Whangbo, M.-H. Organic Superconductors; Prentice-Hall: New Jersey, 1992.
12. Triki, S.; Ouahab, L.; Halet, J.-F.; Pe-a, O.; Padiou, J.; Grandjean, D.; Garrigou-Lagrange, C.; Delhaes, P. J. Chem. Soc., Dalton Trans. 1992, 1217.
13. A preliminary communication has been published: Takimiya, K.; Shibata, Y.; Imaniura, K.; Kashihara, A.; Aso, Y.; Otsubo, T.; Ogura, F. Tetrahedron Lett. 1995, 36, 5045.
14. Sugawara and coworkers reported an independent synthesis of 6a and 6b: Tanabe, J.; Kudo, T.; Okamoto, M.; Kawada, Y.; Ono, G.; Izuoka, A.; Sugawara, T. Chem. Lett. 1995, 579. Tanabe, J.; Ono, G.; Izuoka, A.; Sugawara, T.; Kudo, T.; Saito, T.; Okamoto, M.; Kawada, Y. Mol. Cryst. Liq. Cryst., in press. They also reported preliminary X-ray crystal analyses of 6a and 6b: Tanabe, J.; Ono, G.; Izuoka, A.; Sugawara, T.; Kudo, T.; Saito, T.; Kawada, Y. Abstracts of papers; 1995 Symposium on Molecular Structure, Sendai; the Chemical Society of Japan: Tokyo, Japan, 1995; Abstract 3P092.
15. Sugawara and coworkers reported an independent synthesis of 6a and 6b: Tanabe, J.; Kudo, T.; Okamoto, M.; Kawada, Y.; Ono, G.; Izuoka, A.; Sugawara, T. Chem. Lett. 1995, 579. Tanabe, J.; Ono, G.; Izuoka, A.; Sugawara, T.; Kudo, T.; Saito, T.; Okamoto, M.; Kawada, Y. Mol. Cryst. Liq. Cryst., in press. They also reported preliminary X-ray crystal analyses of 6a and 6b: Tanabe, J.; Ono, G.; Izuoka, A.; Sugawara, T.; Kudo, T.; Saito, T.; Kawada, Y. Abstracts of papers; 1995 Symposium on Molecular Structure, Sendai; the Chemical Society of Japan: Tokyo, Japan, 1995; Abstract 3P092.
16. Sugawara and coworkers reported an independent synthesis of 6a and 6b: Tanabe, J.; Kudo, T.; Okamoto, M.; Kawada, Y.; Ono, G.; Izuoka, A.; Sugawara, T. Chem. Lett. 1995, 579. Tanabe, J.; Ono, G.; Izuoka, A.; Sugawara, T.; Kudo, T.; Saito, T.; Okamoto, M.; Kawada, Y. Mol. Cryst. Liq. Cryst., in press. They also reported preliminary X-ray crystal analyses of 6a and 6b: Tanabe, J.; Ono, G.; Izuoka, A.; Sugawara, T.; Kudo, T.; Saito, T.; Kawada, Y. Abstracts of papers; 1995 Symposium on Molecular Structure, Sendai; the Chemical Society of Japan: Tokyo, Japan, 1995; Abstract 3P092.
17. Steimecke, G.; Sieler, H.-J.; Kirmse, R.; Hoyer, E. Phosphorus Sulphur 1979, 7, 49.
18. Moore, A. J.; Bryce, M. R. J. Chem. Soc., Chem. Commun. 1991, 1639. Hansen, T. K.; Jørgensen, T.; Jensen, F.; Thygesen, P. H.; Christiansen, K.; Hursthouse, M. B.; Harman, M. E.; Malik, M. A.; Girmay, B.; Underbill, A. E.; Begtrup, M.; Kilburn, J. D.; Belmore, K.; Roepstorff, P.; Becher, J. J. Org. Chem. 1993, 58, 1359.
19. Moore, A. J.; Bryce, M. R. J. Chem. Soc., Chem. Commun. 1991, 1639. Hansen, T. K.; Jørgensen, T.; Jensen, F.; Thygesen, P. H.; Christiansen, K.; Hursthouse, M. B.; Harman, M. E.; Malik, M. A.; Girmay, B.; Underbill, A. E.; Begtrup, M.; Kilburn, J. D.; Belmore, K.; Roepstorff, P.; Becher, J. J. Org. Chem. 1993, 58, 1359.
20. Keehn, P. M.; Rosenfeld, S. M. Cyclophanes; Academic Press, New York, 1983; Vols. I and II.
21. Ferguson, J. Chem. Rev. 1986, 86, 958.
22. Tani, K.; Seo, H.; Maeda, M.; Imagawa, K.; Nishiwaki, N.; Ariga, M.; Tohda, Y.; Higuchi, H.; Kuma, H. Tetrahedron Lett. 1995, 36, 1883.
23. 10,14]hexacosa-1(23),10(14)-diene-12,25-dione, mediated by triethyl phosphite.
24. Röhrich, J.; Wolf, P.; Enkelmann, V.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1988, 27, 1377.
25. Kux, U.; Iyoda, M. Chem. Lett. 1994, 2327.