The photochemistry of a potential diphenylsilylene precursor. Time-resolved spectroscopic studies of the reactivity of a transient vinylsilirane

Silicon Chemistry

Volumn 3, Issue 3-4, 2007, Pages 139-149

  Leigh, William J ^a   Huck, Lawrence A ^a   Held, Erica ^a   Harrington, Cameron R ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

1 silacyclopent 3 ene; Kinetics; Photochemistry; Silylene; Vinylgermirane; Vinylsilirane

Indexed keywords

EID: 33845994755     PISSN: 15690660     EISSN: 15728994     Source Type: Journal    
DOI: 10.1007/s11201-006-9017-4     Document Type: Article

References (49)

1. Gaspar, P.P. & West, R. 1998 in Z. Rappoport & Y. Apeloig (eds), The Chemistry of Organic Silicon Compounds, Vol. 2, New York, p. 2463.
2. Weidenbruch, M. 1994 Coord. Chem. Rev. 130, 275.
3. Driess, M. & Grützmacher, H. 1996 Angew. Chem. Int. Ed. Engl. 35, 828.
4. Tokitoh, N. & Okazaki, R. 2000 Coord. Chem. Rev. 210, 251.
5. (a) Becerra, R. & Walsh, R. 1995 Res. Chem. Kinetics 3, 263; and references cited therein. (b) Becerra, R., Cannady, J.P. & Walsh, R. 1999 J. Phys. Chem. A 103, 4457. (c) Becerra, R., Cannady, J.P. & Walsh, R. 2001 Phys. Chem. Chem. Phys. 3, 2343. (d) Alexander, U.N., King, K.D. & Lawrance, W.D. 2001 Phys. Chem. Chem. Phys. 3, 3085. (e) Al-Rubaiey, N., Becerra, R. & Walsh, R. 2002 Phys. Chem. Chem. Phys. 4, 5072. (f) Alexander, U.N., King, K.D. & Lawrance, W.D. 2002 J. Phys. Chem. A 106, 973. (g) Becerra, R., Cannady, J.P. & Walsh, R. 2003 J. Phys. Chem. A 107, 11049. (h) Becerra, R., Cannady, J.P. & Walsh, R. 2004 J. Phys. Chem. A 108, 3987.
6. Baggott, J.E., Blitz, M.A., Frey, H.M. & Walsh, R. 1990 J. Am. Chem. Soc. 112, 8337.
7. (a) Baggott, J.E., Blitz, M.A., Frey, H.M., Lightfoot, P.D. & Walsh, R. 1987 Chem. Phys. Lett. 135, 39. (b) Baggott, J.E., Blitz, M.A., Frey, H.M., Lightfoot, P.D. & Walsh, R. 1988 J. Chem. Soc., Faraday Trans. 2 84, 515.
8. Baggott, J.E., Blitz, M.A., Frey, H.M., Lightfoot, P.D. & Walsh, R. 1992 Internat. J. Chem. Kinet. 24, 127.
9. Levin, G., Das, P.K. & Lee, C.L. 1988 Organometallics 7, 1231.
10. Shizuka, H., Tanaka, H., Tonokura, K., Murata, K., Hiratsuka, H., Ohshita, J. & Ishikawa, M. 1988 Chem. Phys. Lett. 143, 225.
11. Levin, G., Das, P.K., Bilgrien, C. & Lee, C.L. 1989 Organometallics 8, 1206.
12. Yamaji, M., Hamanishi, K., Takahashi, T. & Shizuka, H. 1994 J. Photochem. Photobiol. A: Chem. 81, 1.
13. Conlin, R.T., Netto-Ferreira, J.C., Zhang, S. & Scaiano, J.C. 1990 Organometallics 9, 1332.
14. Gaspar, P.P., Boo, B.H., Chari, S., Ghosh, A.K., Holten, D., Kirmaier, C. & Konieczny, S. 1984 Chem. Phys. Lett. 105, 153.
15. Gaspar, P.P., Holten, D., Konieczny, S. & Corey, J.Y. 1987 Acc. Chem. Res. 20, 329.
16. Konieczny, S., Jacobs, S.J., Braddock Wilking, J.K. & Gaspar, P.P. 1988 J. Organomet. Chem. 341, C17.
17. Michalczyk, M.J., Fink, M.J., De Young, D.J., Carlson, C.W., Welsh, K.M., West, R. & Michl, J. 1986 Silicon, Germanium, Tin and Lead Compounds 9, 75.
18. Ishikawa, M., Nakagawa, K.-I., Enokida, R. & Kumada, M. 1980 J. Organomet. Chem. 201, 151.
19. Kira, M., Miyazawa, T., Koshihara, S., Segawa, Y. & Sakurai, H. 1995 Chem. Lett. 1995, 3.
20. Miyazawa, T., Koshihara, S.Y., Liu, C., Sakurai, H. & Kira, M. 1999 J. Am. Chem. Soc. 121, 3651.
21. Leigh, W.J. & Sluggett, G.W. 1994 Organometallics 13, 269.
22. Kira, M., Ishida, S., Iwamoto, T. & Kabuto, C. 1999 J. Am. Chem. Soc. 121, 9722.
23. Leigh, W.J., Harrington, C.R. & Vargas-Baca, I. 2004 J. Am. Chem. Soc. 126, 16105.
24. Leigh, W.J. & Harrington, C.R. 2005 J. Am. Chem. Soc. 127, 5084.
25. Steinmetz, M.G. & Yu, C. 1992 Organometallics 11, 2686.
26. Jiang, P. & Gaspar, P.P. 2001 J. Am. Chem. Soc. 123, 8622.
27. Ishikawa, M., Ohi, F. & Kumada, M. 1975 J. Organomet. Chem. 86, C23.
28. Ishikawa, M., Nakagawa, K.-I. & Kumada, M. 1979 J. Organomet. Chem. 178, 105.
29. Tortorelli, V.J., Jones, M., Jr., Wu, S. & Li, Z. 1983 Organometallics 2, 759.
30. Kira, M., Taki, T. & Sakurai, H. 1989 J. Org. Chem. 54, 5647.
31. Takahashi, M. 2005 J. Phys. Chem. A 109, 11902.
32. For a discussion of the regiochemistry of the methanolysis of silirane derivatives under various conditions, see Bodnar, P.M., Palmer, W.S., Ridgway, B.H., Shaw, J.T., Smitrovich, J.H. & Woerpel, K.A. 1997 J. Org. Chem. 62, 4737.
33. Zhang, S., Wagenseller, P.E. & Conlin, R.T. 1991 J. Am. Chem. Soc. 113, 4278.
34. Leigh, W.J., Dumbrava, I.G. & Lollmahomed, F. 2006 Can. J. Chem. 84, 934
35. 2 by this route should be revealed in flash photolysis experiments by a fast growth component in the transient absorption due to the germylene and a rapidly decaying prompt signal at 285nm due to 11a. The germylene signals do, in fact, generally exhibit a distinct (50-80ns) growth that lags slightly behind the laser pulse; the transient absorptions in the 270-300nm range are very difficult to sort out because they consist of contributions from at least three species of varying lifetimes [23]. Subsequent studies of the reactions of GeMePh with isoprene and DMB indicate that the forward rate constants are similar for the two dienes, but the equilibrium constant for addition to DMB is significantly lower than that for addition to isoprene [34]. This suggests that the rate constants for dissociation of DMB-derived vinylgermiranes are somewhat greater than those of isoprene-derived derivatives, all else being equal. It is thus possible that the fast growth component of the germylene signals observed in flash photolysis experiments with 1 and related derivatives is due to formation of the germylene by this route, with the growth component appearing faster than it really is due to its superposition on the relatively fast subsequent decay of the germylene due to dimerization.
36. Bobbitt, K.L., Maloney, V.M. & Gaspar, P.P. 1991 Organometallics 10, 2772.
37. Bobbitt, K.L., Lei, D., Maloney, V.M., Parker, B.S., Raible, J.M. & Gaspar, P.P. 1993 in Proceedings of the VIIth International Conference on the Organometallic and Coordination Chemistry of Germanium, Tin and Lead, Riga, p. 41.
38. Walsh, R. 1989 in S. Patai & Z. Rappoport (eds), The Chemistry of Organic Silicon Compounds. p. 371.
39. Grev, R.S., Schaefer, H.F., III & Baines, K.M. 1990 J. Am. Chem. Soc. 112, 9458.
40. Leigh, W.J., Lollmahomed, F. & Harrington, C.R. 2006 Organometallics 25, 2055.
41. Becerra, R., Harrington, C.R., Gaspar, P.P., Leigh, W.J., Vargas-Baca, I., Walsh, R. & Zhou, D. 2005 J. Am. Chem. Soc. 127, 17469.
42. Masamune, S., Murakami, S., Tobita, H. & Williams, D.J. 1983 J. Am. Chem. Soc. 105, 7776.
43. Lei, D., Hwang, R.-J. & Gaspar, P.P. 1984 J. Organomet. Chem. 271, 1.
44. Lei, D. and Gaspar, P.P. 1985 J. Chem. Soc., Chem. Commun. 1985, 1149.
45. Kang, S.-H., Han, J.S., Lee, M.E., Yoo, B.R. & Jung, I.N. 2003 Organometallics 22, 2551.
46. Ohshita, J., Taketsugu, R., Nakahara, Y. & Kunai, A. 2004 J. Organomet. Chem. 689, 3258.
47. Filleux-Blanchard, M.L., An, N.D. & Manuel, G. 1977 J. Organomet. Chem. 137, 11.
48. Rieke, R.D. & Xiong, G. 1991 J. Org. Chem. 56, 3109.
49. Toltl, N.P., Stradiotto, M.J., Morkin, T.L. & Leigh, W.J. 1999 Organometallics 18, 5643.