The differing modes of reaction of 1-(8-dimethylamino-1-naphthyl)-1-hydrodisilane and 1-(1-naphthyl)-1-hydrodisilane in nickel-catalyzed reactions with acetylene: Formation of a pseudo-pentacoordinate silole via Si-Si bond cleavage vs. hydrosilation without Si-Si bond cleavage

Journal of Organometallic Chemistry

Volumn 521, Issue 1-2, 1996, Pages 325-334

  Tamao, Kohei ^a   Asahara, Masahiro ^a   Kawachi, Atsushi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030598762     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-328X(96)06321-8     Document Type: Article

References (43)

1. [1] Reviews: (a) C. Chuit, R.J.P. Corriu, C. Rey and C.J. Young, Chem. Rev., 93 (1993) 1371;
2. (b) G.F. Lanneau, Main Group Chem. News, 1 (1993) 16;
3. (c) R.J.P. Corriu and J.C. Young, in S. Patai and Z. Rappoport (eds.), The Chemistry of Organic Silicon Compounds, Part 2, Wiley, Chichester, UK, 1989, Chapter 20.
4. [2] (a) U. Schubelt, M. Wiener and F.H. Köhler, Chem. Ber., 112 (1979) 708. Anionic pentacoordinate disilane:
5. (b) M. Kira, K. Sato, C. Kabuto and H. Sakurai, J. Am. Chem. Soc., 111 (1989) 3747. Hexacoordinate disilane:
6. (c) G. Sawitzki and H.G. von Schnering, Chem. Ber., 109 (1976) 3728.
7. (d) D. Kummer, A. Balkir and H. Köster, J. Organomet. Chem., 178 (1979) 29.
8. [3] K. Tamao, Y. Tarao, Y. Nakagawa, K. Nagata and Y. Ito, Organometallics, 12 (1993) 1113.
9. [4] K. Tamao, K. Nagata, M. Asahara, A. Kawachi, Y. Ito and M. Shiro, J. Am. Chem. Soc., 117 (1995) 11592.
10. [5] (a) J. Belzner, J. Organomet. Chem., 430 (1992) C51;
11. (b) J. Belzner and H. Ihmels, Tetrahedron Lett., 34 (1993) 6541;
12. (c) J. Belzner, H. Ihmels, B.O. Kneisel and R.H. Irmer, J. Chem. Soc., Chem. Commun., (1994) 1989;
13. (d) J. Belzner, U. Dehnert and D. Stalke, Angew. Chem., Int. Ed. Engl., 33 (1994) 2450;
14. (e) J. Belzner, H. Ihmels and M. Noltemeyer, Tetrahedron Lett., 36 (1995) 8187.
15. [6] (a) G. van Koten, A.J. Leusink and J.G. Noltes, J. Organomet. Chem., 84 (1975) 117;
16. (b) J.T.B.M. Jastrzebski, C.T. Knapp and G. van Koten, J. Organomet. Chem., 255 (1983) 287.
17. [7] K. Tamao, M. Asahara and A. Kawachi, unpublished results.
18. [8] C. Breliere, F. Carre, R.J.P. Corriu, M. Poirier and G. Royo, Organometallics, 5 (1986) 388.
19. [9] K. Tamao, T. Hayashi, Y. Ito and M. Shiro, Organometallics, 11 (1992) 2099.
20. [10] W.S. Sheldrick, in S. Patai and Z. Rappoport (eds.), The Chemistry of Organic Silicon Compounds, Part I, Wiley, Chichester, UK, 1989, Chapter 3.
21. [11] B.J. Helmer, R. West, R.J.P. Corriu, M. Poitier, G. Royo and A. De Saxce, J. Organomet. Chem., 251 (1983) 285.
22. [12] H.K. Sharma and K.H. Pannell, Chem. Rev., 95 (1995) 1351.
23. [13] H. Okinoshina, K. Yamamoto and M. Kumada, J. Am. Chem. Soc., 94 (1972) 9263.
24. [14] Quite recently, Corriu and coworkers have also reported the formation of a potentially pentacoordinate silole having a 2-(dimethylaminomethyl)phenyl group on silicon: B.P.S. Chauhan, R.J.P. Corriu, G.F. Lanneau and C. Priou, Organometallics, 14 (1995) 1657.
25. [15] Thermal degradation of 1 occurred at 145°C in xylene for 68 h to give a methyldiphenylsilane in 28% yield, together with 47% recovery of 1. In contrast, no reaction was observed with 3 under similar conditions.
26. [16] (a) L.S. Chang, M.P. Johnson and M.J. Fink, Organometallics, 8 (1989) 1369;
27. (b) H. Yamashita, M. Tanaka and M. Goto, Organometallics, 1 (1992) 3227;
28. (c) D. Seyferth, M.L. Shannon, S.C. Vick and T.F.O. Lim, Organometallics, 4 (1985) 57;
29. (d) J. Ohshita, Y. Isomura and M. Ishikawa, Organometallics, 8 (1989) 2050.
30. [17] M. Kumada and K. Tamao, Adv. Organomet. Chem., 6 (1968) 19.
31. [18] (a) J.C. Brunet and C. Lemahieu, J. Organomet. Chem., 49 (1973) 381;
32. (b) J. Dubac, A. Laporterie and G. Manuel, Chem. Rev., 90 (1990) 215.
33. [19] (a) K. Tamao, S. Yamaguchi, Y. Ito, Y. Matsuzaki, T. Yamabe, M. Fukushima and S. Mori, Macromolecules, 28 (1995) 8668;
34. (b) V.N. Khabasesku, V. Balaji, S.E. Boganov, O.M. Nefedov and J. Michl, J. Am. Chem. Soc., 116 (1994) 320.
35. [20] F.H. Caye, R.J.P. Corriu, B.J.L. Henner and W.W.C. Wong Chi Man, J. Organomet. Chem., 347 (1988) C1.
36. [21] (a) K. Tamao, A. Kawachi and Y. Ito, Organometallics, 12 (1993) 580;
37. (b) K. Tamao, G.-R. Sun and A. Kawachi, submitted to Organometallics.
38. [22] A.G. Brook, K.H. Pannel and D.G. Anderson, J. Am. Chem. Soc., 90 (1968) 4374.
39. [23] (a) G. Chandra, P.Y. Lo, P.B. Hitchcock and M.F. Lappert, Organometallics, 6 (1987) 191;
40. (b) P.B. Hitchcock, M.F. Lappert and N.J.W. Warhurst, Angew. Chem., Int. Ed. Engl., 30 (1991) 438.
41. [24] PATTY: P.T. Beurskens, G. Admiraal, G. Beurskens, W.P. Bosman, S. Garcia-Granda, R.O. Gould, J.M.M. Smits and C. Smykalla, The DIRDIF program system,Tech. Rep. of the Crystallography Laboratory, University of Nijmgen, Netherlands, 1992.
42. [25] DIRDIF92: P.T. Beurskens, G. Admiraal, G. Beurskens, W.P. Bosman, S. Garcia-Granda, R.O. Gould, J.M.M. Smits and C. Smykalla, The DIRDIF program system, Tech. Rep. of the Crystallography Laboratory, University of Nijmgen, Netherlands, 1992.
43. [26] SAPI91: Fan Hai-Fu, Structure Analysis Programs with Intelligent Control, Rigaku Corp., Tokyo, Japan, 1991.