Silole polymer and cyclic hexamer catenating through the ring silicons

Journal of the American Chemical Society

Volumn 121, Issue 12, 1999, Pages 2937-2938

  Yamaguchi, Shigehiro ^a   Jin, Ren Zhi ^a   Tamao, Kohei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROFORM; CYCLOPENTADIENE DERIVATIVE; LITHIUM; POLYMER; SILANE DERIVATIVE; SILICON DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; FLUORESCENCE SPECTROSCOPY; POLYMERIZATION; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0033620404     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983349j     Document Type: Article

References (22)

1. Recent reviews for siloles: (a) Dubac, J.; Laporterie, A.; Manuel, G. Chem. Rev. 1990, 90, 215. (b) Colomer, E.; Corriu, R. J. P.; Lheureux, M. Chem. Rev. 1990, 90, 265. (c) Dubac, J.; Guerin, C.; Meunier, P. The Chemistry of Organic Silicon Compounds, Rappoport, Z.; Apeloig, Y., Eds.; John Wiley & Sons: 1998; Vol. 2, Chapler 34. (d) Yamaguchi, S.; Tamao, K. J. Chem. Soc., Dalton Trans. 1998, 3693.
2. Recent reviews for siloles: (a) Dubac, J.; Laporterie, A.; Manuel, G. Chem. Rev. 1990, 90, 215. (b) Colomer, E.; Corriu, R. J. P.; Lheureux, M. Chem. Rev. 1990, 90, 265. (c) Dubac, J.; Guerin, C.; Meunier, P. The Chemistry of Organic Silicon Compounds, Rappoport, Z.; Apeloig, Y., Eds.; John Wiley & Sons: 1998; Vol. 2, Chapler 34. (d) Yamaguchi, S.; Tamao, K. J. Chem. Soc., Dalton Trans. 1998, 3693.
3. Recent reviews for siloles: (a) Dubac, J.; Laporterie, A.; Manuel, G. Chem. Rev. 1990, 90, 215. (b) Colomer, E.; Corriu, R. J. P.; Lheureux, M. Chem. Rev. 1990, 90, 265. (c) Dubac, J.; Guerin, C.; Meunier, P. The Chemistry of Organic Silicon Compounds, Rappoport, Z.; Apeloig, Y., Eds.; John Wiley & Sons: 1998; Vol. 2, Chapler 34. (d) Yamaguchi, S.; Tamao, K. J. Chem. Soc., Dalton Trans. 1998, 3693.
4. Recent reviews for siloles: (a) Dubac, J.; Laporterie, A.; Manuel, G. Chem. Rev. 1990, 90, 215. (b) Colomer, E.; Corriu, R. J. P.; Lheureux, M. Chem. Rev. 1990, 90, 265. (c) Dubac, J.; Guerin, C.; Meunier, P. The Chemistry of Organic Silicon Compounds, Rappoport, Z.; Apeloig, Y., Eds.; John Wiley & Sons: 1998; Vol. 2, Chapler 34. (d) Yamaguchi, S.; Tamao, K. J. Chem. Soc., Dalton Trans. 1998, 3693.
5. Review for polysilanes: Miller, R. D.; Michl, J. Chem. Rev. 1989, 89, 1359.
6. Yamaguchi, Y. Synth. Met. 1996, 82, 149.
7. Yamaguchi, S.; Tamao, K. Bull. Chem. Soc. Jpn. 1996, 69, 2327.
8. Yamaguchi, S.; Jin, R.-Z.; Tamao, K.; Shiro, M. Organometallics 1997, 16, 2486.
9. Kanno, K.; Ichinohe, M.; Kabuto, C.; Kira, M. Chem. Lett. 1998, 99.
10. Sanji, T.; Sakai, T.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1998, 120, 4552.
11. Chauhan, B. P. S.; Shimizu, T.; Tanaka, M. Chem. Lett. 1997, 785.
12. Poly(1,1-silole) consisting of 2,3,4,5-tetraphenylsilole units has recently been prepared by R. West and co-workers: Sohn, H.; Huddleston, R.; Powell, D. R.; West, R.; Oka, K.; Yonghua, X. J. Am. Chem. Soc. 1999, 121, 2935.
13. 3, or water, all of which gave almost the same molecular weight polymers.
14. n, = 6000 (n ≈ 19) according to the GPC approximation, which is almost the same as that alter reprecipitation twice from i-PrOH.
15. 29Si NMR become larger as the molecular weights of the polymer become lower, indicating that the peaks are ascribed to the terminal silole rings. The spectra of 2 and 2′ are shown in the Supporting Information.
16. 6 C. 83.48; H, 7.64. Found C, 83.19; H, 7.65.
17. w = 0.082, and GOF = 1.23. Hydrogen atoms were included but not refined.
18. 6: Li, H.; Butler, I. S.; Harrod, J. F. Organometallics 1993, 12, 4553.
19. For the formation of the polymer, the size of the 2,5-substituents is critical. When 2,5-bis(trimethylsilyl)-3,4-diphenyl-1,1-dichlorosilole was empolyed in place of the 2,5-dimethyl derivative 1, the Wurtz-type coupling using Li only gave silole dimers due to the steric congestion.
20. (a) Yamaguchi, S.; Jin, R.-Z.; Tamao, K.; Shiro, M. Organometallics 1997, 16, 2230.
21. (b) Tamao, K.; Yamaguchi, S.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 11715.
22. For the preparation of compound 5, see the Supporting Information.