Reactivity of an aryl-substituted silicon-silicon triple bond: Reactions of a 1,2-diaryldisilyne with alkenes

Journal of the American Chemical Society

Volumn 132, Issue 8, 2010, Pages 2546-2547

  Han, Joon Soo ^a   Sasamori, Takahiro ^a   Mizuhata, Yoshiyuki ^a   Tokitoh, Norihiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEX PRODUCTS; CYCLOHEXENES; ETHYLENE-BRIDGED; SILACYCLOPROPANE; TRIPLE BONDS;

BUTADIENE;

ETHYLENE;

ALKENE; SILICON;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; CYCLIZATION; CYCLOADDITION;

EID: 77950376942     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja9108566     Document Type: Article

References (29)

1. (a) West, R.; Fink, M. J.; Michl, J. Science 1981, 214, 1343.
2. (b) Kira, M.; Iwamoto, T. Adv. Organomet. Chem. 2006, 54, 73.
3. Sasamori, T.; Tokitoh, N. In Encyclopedia of Inorganic Chemistry, 2nd ed.; King, R. B., Ed.; John Wiley & Sons: Chichester, U.K., 2005; p 1698.
4. Weidenbruch, M. In The Chemistry of Organic Silicon Compounds, Vol. 3; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons: Chichester, U.K., 2001; p 391.
5. (e) West, R. Polyhedron 2002, 2I, 467.
6. (a) Sekiguchi, A.; Kinjo, R.; Ichinohe, M. Science 2004, 305, 1755.
7. (b) Wiberg, N.; Vasisht, S. K.; Fischer, G.; Mayer, P. Z. Anorg. Allg. Chem. 2004, 630, 1823.
8. (a) Kobayashi, K.; Nagase, S. Organometallics 1997, 16, 2489.
9. (b) Nagase, S.; Kobaysahi, K.; Takagi, N. J. Organomet. Chem. 2000, 611, 264.
10. Sasamori, T.; Hironaka, K.; Sugiyama, Y.; Takagi, N.; Nagase, S.; Hosoi, Y.; Furukawa, Y.; Tokitoh, N. J. Am. Chem. Soc. 2008, 130, 13856.
11. (a) Sekiguchi, A.; Ichinohe, M.; Kinjo, R. Bull. Chem. Soc. Jpn. 2006, 79, 825.
12. (b) Kinjo, R.; Ichinohe, M.; Sekiguchi, A. J. Am. Chem. Soc. 2007, 129, 26.
13. Kinjo, R.; Ichinohe, M.; Sekiguchi, A.; Takagi, N.; Sumimoto, M.; Nagase, S. J. Am, Chem. Soc. 2007, 129, 7766.
14. Takeuchi, K; Ichinohe, M.; Sekiguchi, A. J. Am. Chem. Soc. 2008, 130, 16848.
15. (e) Takeuchi, K.; Ichinohe, M.; Sekiguchi, A.; Guo, J.-D.; Nagase, S. Organometallics 2009, 28, 2658.
16. For recent reviews of dimetallynes, see: (a) Power, P. P. Appl. Organomet. Chem. 2005, 19, 488.
17. (b) Power, P. P. Oreanometallics 2007. 26, 4362.
18. (a) Stender, M.; Phillips, A. D.; Power, P. P. Chem. Commun. 2002, 1312.
19. (b) Pu, L.; Philips, A. D.; Richards, A. F.; Stender, M.; Simons, R. S.; Olmstead, M. M.; Power, P. P. J. Am. Chem. Soc. 2003, 125, 11626.
20. Spikes, G. H.; Fettinger, J. C.; Power, P. P. J. Am. Chem. Soc. 2005, 127, 12232.
21. Cui, C.; Olmstead, M. M.; Fettinger, J. C.; Spikes, G. H.; Power, P. P. J. Am. Chem. Soc. 2005, 127, 17530.
22. (e) Sugiyama, Y.; Sasamori, T.; Hosoi, Y.; Furukawa, Y.; Takagi, N.; Nagase, S.; Tokitoh, N. J. Am. Chem. Soc. 2006, 128, 1023.
23. (f) Peng, Y.; Ellis, B. D.; Wang, X.; Fettinger, J. C.; Power, P. P. Science 2009, 325, 1668.
24. (a) Tokitoh, N.; Suzuki, H.; Okazaki, R.; Ogawa, K. J. Am. Chem. Soc. 1993, 115, 10428.
25. (b) Takeda, N.; Tokitoh, N. Synlett 2007, 2483, and references therein.
26. (a) Suzuki, H.; Tokitoh, N.; Okazaki, R.; Harada, J.; Ogawa, K.; Tomoda, S.; Goto, M. Organometallics 1995, 14, 1016.
27. (b) Wiberg, N.; Auer, H.; Nöth, H.; Knizek, J.; Polbom. K Angew. Chem., Int. Ed. 1998, 37, 2869.
28. Boomgaarden, S.; Saak, W.; Marsmann, H.; Weidenbruch, M. Z. Anorg. Allg. Chem. 2002, 628, 1745.
29. The exceptional structural features will be discussed in detail elsewhere.