Phosphine-Catalyzed Si-C Coupling of Bissilylmethanes: Preparation of Cyclic (Cl2SiCH2)2 and Linear Cl 2Si(CH2SiCl3)2 via Silylene and Silene Intermediates

Organometallics

Volumn 29, Issue 3, 2010, Pages 687-691

  Hong, Soon Hyun ^a,b   Hyun, Sang Il ^a,b   Jung, Il Nam ^a,b   Han, Won Sik ^a   Kim, Min Hye ^a   Yun, Hoseop ^c   Nam, Suk Woo ^d   Kang, Sang Ook ^a  

^a Korea University   (South Korea)

^b Megacenter SK Technopark   (South Korea)

^c Ajou University   (South Korea)

^d Korea Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

C-COUPLING REACTIONS; CARBOSILANES; METHYLENE CHLORIDE; PRODUCT ISOLATION; REACTION PATHWAYS; SILYLENES;

DICHLOROMETHANE; PHOSPHORUS COMPOUNDS;

SILICON;

EID: 76149114609     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om901071k     Document Type: Article

References (40)

1. (a) Seyferth, D. Inorganic and Organometallic Polymers; ACS Symposium Series 360; ACS:'Washington, DC, 1988;
2. Chapter 3. (b) Birot, M; Pilot, J. P.; Dunogues, J. Chem. Rev 1995, 95, 1443.
3. (c) Corriu, R. J. P.; Enders, M.; Huille, S.; Moreau, J. J. E. Chem. Mater. 1994, 6, 15.
4. (d) Laine, R. M.; Babonneau, F. Chem. Mater. 1993, 5, 260.
5. (a) Bobrovsky, A. Y.; Pakhomov, A. A.; Zhu, X.-M.; Boiko, N. I.; Shibaev, V. P.; Stumpe, J. J. Phys. Chem. B 2002, 106, 540.
6. (b) Li, C. F.; Jin, F.; Dong, X. Z.; Chen, W. Q.; Duan, X. M. J. Lumin. 2007, 127, 321.
7. (a) Ohshita, J.; Matsuguchi, A.; Furumori, K.; Hong, R. F.; Ishikawa, M. Macromolecules 1992, 25, 2134.
8. (b) Brefort, J. L.; Corriu, R. J. P.; Gerbier, P.; Guerin, C.; Henner, B. J. L.; Jean, A.; Kuhlmann, Th; Gamier, F.; Yassar, A. Organometallics 1992, 11, 2500.
9. (a) Son, H. J.; Han, W. S.; Lee, K. H.; Jung, H. J.; Lee, C. M.; Ko, J.; Kang, S. O. Chem. Mater. 2006, 18, 5811.
10. (b) Ohshita, J.; Takata, A.; Kai, H.; Kunai, A.; Komaguchi, K.; Shiotani, M.; Adachi, A.; Okita, K.; Harima, Y.; Kunugi, Y.; Yamashita, K.; Ishikawa, M. Organometallics 2000, 19, 4492.
11. (c) Lee, T.; Jung, I.; Song, K. H.; Baik, C.; Kim, S.; Kim, D.; Kang, S. O.; Ko, J. Organometallics 2004, 23, 4184.
12. (d) Chen, Y.-J.; Luh, T.-Y. Macromolecules 2005, 38, 4563.
13. (a) Petrov, A. D.; Mironov, V. F.; Ponomarenko,V. A.; Chemyshev, E. A. Synthesis of Organosilicon Monomers; Consultants Bureau: New York, 1964.
14. (b) Voorhoeve, R. J. H. Organohalosilanes: Precursors to Silicones; Elsevier: New York, 1967.
15. (c) Lewis, K. M.; Rethwisch, D. G. Catalyzed Direct Reactions of Silicon; Elsevier: Amsterdam, 1993.
16. Petnode, W. I.; Schiessler, R. W. U.S. Patent 2381000, 2381001, 2381002, 1945;
17. Chem. Abstr. 1945, 39, 4889.
18. Fritz, G.; Matern, E. Carbosilanes: Synthesis and Reactions; Springer: New York, 1986; pp 46-53.
19. Fritz, G.; Thielking, H. Z. Anorg. Allg. Chem. 1960, 306, 39.
20. Fritz, G.; Haase, R.; Kummer, D. Z. Anorg. Allg. Chem. 1984, 512, 131.
21. Yeon, S. H.; Han, J. S.; Yoo, B. R.; Jung, I. N. J. Organomet. Chem. 1996, 516, 91.
22. Cho,Y. S.; Kang, S. H.; Han, J. S.; Yoo, B. R.; Jung, I. N. J. Am. Chem. Soc. 2001, 123, 5584.
23. (a) Kang, S. H.; Han, J. S.; Lee, M. H.; Yoo, B. R.; Jung, I. N. Organometallics 2003, 22, 2551.
24. (b) Kang, S. H.; Han, J. S.; Yoo, B. R.; Lee, M. S.; Jung, I. N. Organometallics 2003, 22, 529.
25. (c) Kang, S. H.; Han, J. S.; Lim, W. C.; Jung, I. N.; Lee, M. E.; Yoo, B. R. Organometallics 2006, 25, 318.
26. Jung, I. N.; Yeon, S. H.; Han, J. S. Organometallics 1993, 12, 2360.
27. Firtz, G. Angew. Chem., In. Ed. Engl. 1987, 26, 1111.
28. (a) Irwin, R. M.; Cooke, J. M.; Laane, J. J. Am. Chem. Soc. 1977, 99, 3273.
29. (b) Auner, N.; Grobe, J. J. Organomet. Chem. 1981, 222, 33.
30. (c) Nametkin, N. S.; Vdovin, V. M.; Zav'yalov, V. I.; Grinberg, P. L. Izv. Akad. Nauk. SSSR, Ser. Khim. 1965, 5, 929.
31. Jung, I. N. et al. Unpublished results for the phosphine-catalyzed Si-H/Si-Cl exchange reactions.
32. Fritz, G.; Matern, E. Carbosilanes: Synthesis and Reactions; Springer: New York, 1986; p 218.
33. (a) Dzarnosik, J.; Rickborn, S. F.; O'Neal, H. E.; Ring, M. A. Organometallics 1982, 1, 1217.
34. (b) Rogers, D. S.; O'Neal, H. E.; Ring, M. A. Organometallics 1986, 5, 1467.
35. (a) Berry, M. B.; Griffiths, R. J.; Sanganee, M. J.; Steel, P. G.; Whelligan, D. K. Org. Biomol. Chem. 2004, 2, 2381.
36. (b) Brook, A. G.; Vorsphol, K.; Ford, R. R.; Hesse, M.; Chatterton, W. J. Organometallics 1987, 6, 2128.
37. Davidson, I. M. T.; Wood, I. T. Chem. Commun. 1982, 550.
38. Shriver, D. F.; Drezdon, M. A. Manipulation of Air-Sensitive Compounds, 2nd ed.; Wiley: New York, 1986.
39. (a) SMART and SAINT; Bruker Analytical X-Ray Division: Madison, WI, 2002.
40. (b) Sheldrick, G. M. SHELXTL-PLUS Software Package; Bruker Analytical X-Ray Division: Madison, WI, 2002.