Efficient synthesis of 2-iodo and 2-dicyanomethyl derivatives of thiophene, selenophene, tellurophene, and thieno[3,2-b]thiophene

Heterocycles

Volumn 43, Issue 9, 1996, Pages 1927-1935

  Takahashi, Kazuko ^a   Tarutani, Shinji ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013228409     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-96-7517     Document Type: Article

References (22)

1. 1. K. Takahashi, Pure and Appl. Chem., 1993, 65, 127; S. H. Kawai, S. L. Gilat, and J. -M. Lehn, J. Chem. Soc., Chem. Comm., 1994, 1011; T. Saika, T. Iyoda, K. Honda, and T. Shimidzu, J. Chem. Soc., Chem. Comm., 1992, 591; K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull, Chem. Soc. Jpn., 1989, 62, 1539; K. Takahashi, T. Suzuki, K. Akiyama, Y. Ikegami, and Y. Fukazawa, J. Am. Chem. Soc., 1991, 113, 4576.
2. K. Takahashi, Pure and Appl. Chem., 1993, 65, 127; S. H. Kawai, S. L. Gilat, and J. -M. Lehn, J. Chem. Soc., Chem. Comm., 1994, 1011; T. Saika, T. Iyoda, K. Honda, and T. Shimidzu, J. Chem. Soc., Chem. Comm., 1992, 591; K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull, Chem. Soc. Jpn., 1989, 62, 1539; K. Takahashi, T. Suzuki, K. Akiyama, Y. Ikegami, and Y. Fukazawa, J. Am. Chem. Soc., 1991, 113, 4576.
3. K. Takahashi, Pure and Appl. Chem., 1993, 65, 127; S. H. Kawai, S. L. Gilat, and J. -M. Lehn, J. Chem. Soc., Chem. Comm., 1994, 1011; T. Saika, T. Iyoda, K. Honda, and T. Shimidzu, J. Chem. Soc., Chem. Comm., 1992, 591; K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull, Chem. Soc. Jpn., 1989, 62, 1539; K. Takahashi, T. Suzuki, K. Akiyama, Y. Ikegami, and Y. Fukazawa, J. Am. Chem. Soc., 1991, 113, 4576.
4. K. Takahashi, Pure and Appl. Chem., 1993, 65, 127; S. H. Kawai, S. L. Gilat, and J. -M. Lehn, J. Chem. Soc., Chem. Comm., 1994, 1011; T. Saika, T. Iyoda, K. Honda, and T. Shimidzu, J. Chem. Soc., Chem. Comm., 1992, 591; K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull, Chem. Soc. Jpn., 1989, 62, 1539; K. Takahashi, T. Suzuki, K. Akiyama, Y. Ikegami, and Y. Fukazawa, J. Am. Chem. Soc., 1991, 113, 4576.
5. K. Takahashi, Pure and Appl. Chem., 1993, 65, 127; S. H. Kawai, S. L. Gilat, and J. -M. Lehn, J. Chem. Soc., Chem. Comm., 1994, 1011; T. Saika, T. Iyoda, K. Honda, and T. Shimidzu, J. Chem. Soc., Chem. Comm., 1992, 591; K. Yui, Y. Aso, T. Otsubo, and F. Ogura, Bull, Chem. Soc. Jpn., 1989, 62, 1539; K. Takahashi, T. Suzuki, K. Akiyama, Y. Ikegami, and Y. Fukazawa, J. Am. Chem. Soc., 1991, 113, 4576.
6. 2. V. N. Kalinin, Synthesis, 1992, 413; R. D. McCullough, R. D. Lowe, M. Jayaraman, and D. L. Anderson, J. Org. Chem., 1993, 58, 904.
7. V. N. Kalinin, Synthesis, 1992, 413; R. D. McCullough, R. D. Lowe, M. Jayaraman, and D. L. Anderson, J. Org. Chem., 1993, 58, 904.
8. W. Minns, Org. Synth. Coll. Vol. II, 1950, 357.
9. F. Challenger and R. Emmott, J. Inst. Petrol., London, 1951, 37, 396.
10. After the completion of our present study, a new iodinating reagent of thiophene derivatives was published: M. D'Auria and G. Mauriello, Tetrahedron Lett., 1995, 36, 4883.
11. F. Fringuelli, S. Gronowitz, A. -B. Hörnfeldt, I. Johnson, and A. Taticchi, Acta Chemica Scand., 1976, B 30, 605.
12. 7. K. Takahashi and S. Tarutani, J. Chem. Soc., Chem. Comm., 1994, 519; K. Takahashi and S. Tarutani, Adv. Mater., 1995, 639; K. Takahashi and S. Tarutani, Synth. Metals, 1995, 70, 1165; K. Takahashi, S. Tarutani, and M. Yoshifuji, The 69th Annual Meeting of the Chemical Society of Japan, Kyoto, March, 1995, Abstr. I, p. 437.
13. K. Takahashi and S. Tarutani, J. Chem. Soc., Chem. Comm., 1994, 519; K. Takahashi and S. Tarutani, Adv. Mater., 1995, 639; K. Takahashi and S. Tarutani, Synth. Metals, 1995, 70, 1165; K. Takahashi, S. Tarutani, and M. Yoshifuji, The 69th Annual Meeting of the Chemical Society of Japan, Kyoto, March, 1995, Abstr. I, p. 437.
14. K. Takahashi and S. Tarutani, J. Chem. Soc., Chem. Comm., 1994, 519; K. Takahashi and S. Tarutani, Adv. Mater., 1995, 639; K. Takahashi and S. Tarutani, Synth. Metals, 1995, 70, 1165; K. Takahashi, S. Tarutani, and M. Yoshifuji, The 69th Annual Meeting of the Chemical Society of Japan, Kyoto, March, 1995, Abstr. I, p. 437.
15. K. Takahashi and S. Tarutani, J. Chem. Soc., Chem. Comm., 1994, 519; K. Takahashi and S. Tarutani, Adv. Mater., 1995, 639; K. Takahashi and S. Tarutani, Synth. Metals, 1995, 70, 1165; K. Takahashi, S. Tarutani, and M. Yoshifuji, The 69th Annual Meeting of the Chemical Society of Japan, Kyoto, March, 1995, Abstr. I, p. 437.
16. M. Uno, K. Seto, and S. Takahashi, J. Chem. Soc., Chem. Comm., 1984, 932.
17. S. Gronowitz, I. Johnson, and A. -B. Hornfeldt, Chemica Scripta, 1975, 7, 111.
18. The yield of 7 (7b) becomes much lower by using a less amount of THF (see experimental part).
19. Compound (5a) destroyed gradually in methanol at room temperature.
20. Inconvenient stepwise synthesis of a π-electron system with 2-dicyanomethylene-2,5-dihydrothiophene moiety was reported: K. Takahashi, K. Takase, and T. Sakae, Chem. Lett., 1980, 1485.
21. R. A. Huffman and S. Gronowitz, Arkiv Kemi., 1960, 16, 515.
22. S. Gronowitz and R. A. Hoffman, Arkiv Kemi., 1960, 16, 539.