Synthesis of a 1-hydrosilene stable in solution and its unique properties

Organometallics

Volumn 27, Issue 10, 2008, Pages 2163-2165

  Ozaki, Shuhei ^a   Sasamori, Takahiro ^a   Tokitoh, Norihiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; FARM BUILDINGS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TELLURIUM COMPOUNDS;

(PL) PROPERTIES; DEHYDROFLUORINATION REACTION; FLUOROSILANE; NMR SPECTROS COPY; SYNTHESIS (OF CHIRAL IONIC LIQUIDS); TRIMETHYLSILYL (TMS);

MICROFLUIDICS;

EID: 44649134540     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om8001334     Document Type: Article

References (47)

1. For recent reviews, see: (a) Brook, A. G.; Brook, M. A. Adv. Organomet. Chem. 1996, 39, 71-158.
2. (b) Escudié, J.; Couret, C.; Ranaivonjatovo, H. Coord. Chem. Rev. 1998, 180, 565-592.
3. (c) Morkin, T. L.; Leigh, W. J. Acc. Chem. Res. 2001, 34, 129-136.
4. (d) Gusel'nikov, L. E. Coord. Chem. Rev. 2003, 244, 149-240.
5. (e) Ottosson, H.; Steel, P. G. Chem.-Eur. J. 2006, 12, 1576-1585.
6. (f) Sasamori, T.; Tokitoh, N. Encyclopedia of Inorganic Chemistry, 2nd ed.; King, R. B., Ed.; John Wiley & Sons: Chichester, 2005; pp 1698-1740.
7. Brook, A. G.; Abdesaken, F.; Gutekunst, B.; Gutekunst, G.; Kallury, R. K. J. Chem. Soc., Chem. Commun. 1981, 191-192.
8. Some transition-metal complexes of a hydrosilene have already been reported; see: (a) Mork, B. V.; Tilley, T. D.; Schultz, A. J.; Cowan, J. A. J. Am. Chem. Soc. 2004, 126, 10428-10440.
9. (b) Watanabe, T.; Hashimoto, H.; Tobita, H. Angew. Chem., Int. Ed. 2004, 43, 218-221.
10. (c) Glaser, P. B.; Tilley, T. D. Organometallics 2004, 23, 5799-5812.
11. (d) Watanabe, T.; Hashimoto, H.; Tobita, H. J. Am. Chem. Soc. 2006, 128, 2176-2177.
12. (e) Sakaba, H.; Hirata, T.; Kabuto, C.; Kabuto, K. Organometallics 2006, 25, 5145-5150.
13. (f) Hashimoto, H.; Ochiai, M.; Tobita, H. J. Organomet. Chem. 2007, 692, 36-43.
14. (g) Ochiai, M.; Hashimoto, H.; Tobita, H. Angew. Chem., Int. Ed. 2007, 46, 8192-8194.
15. (a) Maier, G.; Mihm, G.; Reisenauer, H. P. Angew. Chem., Int. Ed. Engl. 1981, 20, 597-598.
16. (b) Rosmus, P.; Bock, H.; Solouki, B.; Maier, G.; Mihm, G. Angew. Chem., Int. Ed. Engl. 1981, 20, 598-599.
17. Recent papers and reviews for the synthesis of novel low-coordinated organosilicon compounds by taking advantage of a Tbt group, see: (a) Okazaki, R.; Tokitoh, N. Acc. Chem. Res. 2000, 33, 625-630.
18. (b) Tokitoh, N.; Okazaki, R. Coord. Chem. Rev. 2000, 210, 251-277.
19. (c) Wakita, K.; Tokitoh, N.; Okazaki, R.; Takagi, N.; Nagase, S. J. Am. Chem. Soc. 2000, 122, 5648-5649.
20. (d) Takeda, N.; Kajiwara, T.; Suzuki, H.; Okazaki, R.; Tokitoh, N. Chem.-Eur. J. 2003, 9, 3530-3543.
21. (e) Kajiwara, T.; Takeda, N.; Sasamori, T.; Tokitoh, N. Chem. Commun. 2004, 2004, 2218-2219.
22. (f) Tokitoh, N. Acc. Chem. Res. 2004, 37, 86-94.
23. (g) Tokitoh, N.; Shinohara, A.; Matsumoto, T.; Sasamori, T.; Takeda, N.; Furukawa, Y. Organometallics 2007, 26, 4048-4053.
24. Sasamori, T.; Ozaki, S.; Tokitoh, N. Chem. Lett. 2007, 36, 588-589.
25. Still, I. W. J.; Kutney, G. W.; Mclean, D. J. Org. Chem. 1982, 47, 555-560.
26. All the new compounds here obtained showed satisfactory spectral data. Experimental procedures and compound data are described in the Supporting Information.
27. 6 solution, and they are in good agreement with the reported data in ref 10.
28. For examples, see: (a) Olah, G. A.; Field, L. D. Organometallics 1982, 1, 1485-1487.
29. (b) Olah, G. A.; Hunadi, R. J. J. Am. Chem. Soc. 1980, 102, 6989-6992.
30. (c) Sollradl, H.; Hengge, E. J. Organomet. Chem. 1983, 243, 257-269.
31. (d) Cox, R. H.; Austin, W. K. J. Organomet. Chem. 1971, 26, 331-334.
32. (e) Jensen, M. A. J. Organomet. Chem. 1968, 11, 423-427.
33. (a) Rastelli, A.; Pozzoli, S. A. J. Mol. Struct. 1973, 18, 463-469.
34. (b) Watanabe, H.; Akaba, R.; Iezumi, T.; Nagai, Y. Bull. Chem. Soc. Jpn. 1980, 53, 2981-2985.
35. Wiberg, N.; Niedermayer, W.; Nöth, H.; Warchhold, M. Z. Anorg. Allg. Chem. 2001, 627, 1717-1722.
36. Kinjo, R.; Ichinohe, M.; Sekiguchi, A. J. Am. Chem. Soc. 2007, 129, 26-27.
37. The structural optimizations were performed by using the Gaussian 03 program at the B3LYP/6-31G(d) level. The calculations for the NMR chemical shifts and coupling constants were performed by using the ADF 2006 program package with TZ2Pae basis sets. The NBO calculations were performed with the NBO 5.0 program. See Supporting Information.
38. (a) Kessler, G.; Kriegsma, H. Z. Anorg. Allg. Chem. 1966, 342, 53-62.
39. (b) Reich, P.; Kriegsma, H. Z. Anorg. Allg. Chem. 1965, 334, 283-291.
40. -3.
41. (a) To our knowledge, no thermal [6+6]-dimerization has been reported so far, though a few reports on the photochemical [6+6]-dimerization of organic π-electron-conjugated systems have been reported. (a) Hao, N.; Sawyer, J. F.; Sayer, B. G.; Mcglinchey, M. J. J. Am. Chem. Soc. 1979, 101, 2203-2204.
42. (b) Mukai, T.; Tezuka, T.; Akasaki, Y. J. Am. Chem. Soc. 1966, 88, 5025-5023.
43. (c) Keil, J. M.; Massa, W.; Riedel, R.; Seitz, G.; Wocadlo, S. Tetrahedron Lett. 1994, 35, 7923-7926.
44. (a) Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 395-397.
45. (b) Hoffmann, R. Angew. Chem., Int. Ed. 2004, 43, 6586-6590, and references therein.
46. It is difficult to draw a conclusion whether the [6+6]-dimerization of 1 proceeded via the concerted or stepwise mechanism. It should be noted that such unusual [6+6]-dimerization of the π-conjugated system containing the Si=C unit was observed.
47. Real molecule models were used for the theoretical calculations. The values shown here are estimated on the basis of the SCF energies calculated at the B3LYP/6-31G(d) level.