7,7,8,8-Tetra(2-thienyl)-p-quinodimethanes. New electron-donating p-quinodimethanes

Chemistry Letters

Volumn , Issue 6, 1999, Pages 519-520

  Kurata, Hiroyuki ^a   Inase, Maki ^a   Oda, Masaji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033241962     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.519     Document Type: Article

References (23)

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10. B. Abarca, G. Asensio, R. Ballesteros, and T. Varea, J. Org. Chem., 56, 3224 (1991); T. Suzuki, H. Shiohara, M. Monobe, T. Sakimura, S. Tanaka, Y. Yamashita, and T. Miyashi, Angew. Chem. Int. Ed. Engl., 31, 455 (1992); T. Kawase, S. Muro, H. Kurata, and M. Oda, J. Chem. Soc., Chem. Commun., 1992, 778; T. Kawase, N. Ueno, and M. Oda, Tetrahedron Lett., 33, 5405 (1992); T. Kawase, H. Kurata, T. Morikawa, and M. Oda, Tetrahedron Lett., 34, 3449 (1993); H. Kurata, M. Monden, T. Kawase, and M. Oda, Tetrahedron Lett., 39, 7135 (1998).
11. B. Abarca, G. Asensio, R. Ballesteros, and T. Varea, J. Org. Chem., 56, 3224 (1991); T. Suzuki, H. Shiohara, M. Monobe, T. Sakimura, S. Tanaka, Y. Yamashita, and T. Miyashi, Angew. Chem. Int. Ed. Engl., 31, 455 (1992); T. Kawase, S. Muro, H. Kurata, and M. Oda, J. Chem. Soc., Chem. Commun., 1992, 778; T. Kawase, N. Ueno, and M. Oda, Tetrahedron Lett., 33, 5405 (1992); T. Kawase, H. Kurata, T. Morikawa, and M. Oda, Tetrahedron Lett., 34, 3449 (1993); H. Kurata, M. Monden, T. Kawase, and M. Oda, Tetrahedron Lett., 39, 7135 (1998).
12. B. Abarca, G. Asensio, R. Ballesteros, and T. Varea, J. Org. Chem., 56, 3224 (1991); T. Suzuki, H. Shiohara, M. Monobe, T. Sakimura, S. Tanaka, Y. Yamashita, and T. Miyashi, Angew. Chem. Int. Ed. Engl., 31, 455 (1992); T. Kawase, S. Muro, H. Kurata, and M. Oda, J. Chem. Soc., Chem. Commun., 1992, 778; T. Kawase, N. Ueno, and M. Oda, Tetrahedron Lett., 33, 5405 (1992); T. Kawase, H. Kurata, T. Morikawa, and M. Oda, Tetrahedron Lett., 34, 3449 (1993); H. Kurata, M. Monden, T. Kawase, and M. Oda, Tetrahedron Lett., 39, 7135 (1998).
13. B. Abarca, G. Asensio, R. Ballesteros, and T. Varea, J. Org. Chem., 56, 3224 (1991); T. Suzuki, H. Shiohara, M. Monobe, T. Sakimura, S. Tanaka, Y. Yamashita, and T. Miyashi, Angew. Chem. Int. Ed. Engl., 31, 455 (1992); T. Kawase, S. Muro, H. Kurata, and M. Oda, J. Chem. Soc., Chem. Commun., 1992, 778; T. Kawase, N. Ueno, and M. Oda, Tetrahedron Lett., 33, 5405 (1992); T. Kawase, H. Kurata, T. Morikawa, and M. Oda, Tetrahedron Lett., 34, 3449 (1993); H. Kurata, M. Monden, T. Kawase, and M. Oda, Tetrahedron Lett., 39, 7135 (1998).
14. Upon addition of alkyllithiums to THF solutions of 3a at low temperature, the solutions turned to deep purple from red and addition of electrophiles mostly resulted in the recovery of 3a.
15. 13 and therefore the present tetrafold trimethylsilylation probably proceeds through stepwise lithiation and trimethylsilylation.
16. 2) δ 175.31, 158.27, 155.83, 150.13, 145.25, 144.62, 138.08, 137.30, 135.31, 130.26, 127.53, 127.38, 126.16, 47.89.
17. 6.
18. Measured under the same conditions for 3a-d (see Table 1).
19. A. Ishi, Y. Horikawa, I. Takaki, J. Shibata, J. Nakayama, and M. Hoshino, Tetrahedron Lett., 32, 4313 (1991).
20. The D:A ratios were determined by elemental analyses and the electrical conductivity was measured on compressed pellets by two-probe technique at room temperature.
21. 14
22. M. Oda, T. Enomoto, T. Kawase, and H. Kurata, Phosphorus, Sulfur, and Silicon, 120 & 121, 401 (1997), and references cited therein.
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