Generation and Trapping of Bis(dialkylamino)silylenes: Experimental Evidence for Bridged Structure of Diaminosilylene Dimers

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 1, 1997, Pages 253-260

  Sakamoto, Kenkichi ^a   Tsutsui, Shinobu ^a   Sakurai, Hideki ^a,b   Kira, Mitsuo ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000084574     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.253     Document Type: Article

References (41)

1. Reviews for silylenes, see: a) P. P. Gasper, "Reactive Intermediates," ed by M. Jones, Jr., and R. T. Moss, John Wiley, New York (1978), Vol. 1, Chap. 7; b) (1981), Vol. 2, Chap. 9; c) (1985), Vol. 3, Chap. 9; d) P. P. Gaspar, D. Holten, and S. Konieczny, Acc. Chem. Res., 20, 329 (1987); e) Y.-N. Tang, "Reactive Intermediates, "ed by R. A. Abramovitch, Plenum Press, New York (1982), Vol. 2, Chap. 4; f) Y. Apeloig, "The Chemistry of Organic Silicon Compounds, "ed by S. Patai and Z. Rappoport, John Wiley, New York (1989), Part 1, Chap. 2; g) O. M. Nefedov, M. P. Egorov, A. I. Ioffe, L. G. Menchikov, P. S. Zuev, V. I. Minkin, B. Ya. Simkin, and M. N. Glukhovtsev, Pure Appl. Chem., 64, 265 (1992).
2. Reviews for silylenes, see: a) P. P. Gasper, "Reactive Intermediates," ed by M. Jones, Jr., and R. T. Moss, John Wiley, New York (1978), Vol. 1, Chap. 7; b) (1981), Vol. 2, Chap. 9; c) (1985), Vol. 3, Chap. 9; d) P. P. Gaspar, D. Holten, and S. Konieczny, Acc. Chem. Res., 20, 329 (1987); e) Y.-N. Tang, "Reactive Intermediates, "ed by R. A. Abramovitch, Plenum Press, New York (1982), Vol. 2, Chap. 4; f) Y. Apeloig, "The Chemistry of Organic Silicon Compounds, "ed by S. Patai and Z. Rappoport, John Wiley, New York (1989), Part 1, Chap. 2; g) O. M. Nefedov, M. P. Egorov, A. I. Ioffe, L. G. Menchikov, P. S. Zuev, V. I. Minkin, B. Ya. Simkin, and M. N. Glukhovtsev, Pure Appl. Chem., 64, 265 (1992).
3. Reviews for silylenes, see: a) P. P. Gasper, "Reactive Intermediates," ed by M. Jones, Jr., and R. T. Moss, John Wiley, New York (1978), Vol. 1, Chap. 7; b) (1981), Vol. 2, Chap. 9; c) (1985), Vol. 3, Chap. 9; d) P. P. Gaspar, D. Holten, and S. Konieczny, Acc. Chem. Res., 20, 329 (1987); e) Y.-N. Tang, "Reactive Intermediates, "ed by R. A. Abramovitch, Plenum Press, New York (1982), Vol. 2, Chap. 4; f) Y. Apeloig, "The Chemistry of Organic Silicon Compounds, "ed by S. Patai and Z. Rappoport, John Wiley, New York (1989), Part 1, Chap. 2; g) O. M. Nefedov, M. P. Egorov, A. I. Ioffe, L. G. Menchikov, P. S. Zuev, V. I. Minkin, B. Ya. Simkin, and M. N. Glukhovtsev, Pure Appl. Chem., 64, 265 (1992).
4. Reviews for silylenes, see: a) P. P. Gasper, "Reactive Intermediates," ed by M. Jones, Jr., and R. T. Moss, John Wiley, New York (1978), Vol. 1, Chap. 7; b) (1981), Vol. 2, Chap. 9; c) (1985), Vol. 3, Chap. 9; d) P. P. Gaspar, D. Holten, and S. Konieczny, Acc. Chem. Res., 20, 329 (1987); e) Y.-N. Tang, "Reactive Intermediates, "ed by R. A. Abramovitch, Plenum Press, New York (1982), Vol. 2, Chap. 4; f) Y. Apeloig, "The Chemistry of Organic Silicon Compounds, "ed by S. Patai and Z. Rappoport, John Wiley, New York (1989), Part 1, Chap. 2; g) O. M. Nefedov, M. P. Egorov, A. I. Ioffe, L. G. Menchikov, P. S. Zuev, V. I. Minkin, B. Ya. Simkin, and M. N. Glukhovtsev, Pure Appl. Chem., 64, 265 (1992).
5. Reviews for silylenes, see: a) P. P. Gasper, "Reactive Intermediates," ed by M. Jones, Jr., and R. T. Moss, John Wiley, New York (1978), Vol. 1, Chap. 7; b) (1981), Vol. 2, Chap. 9; c) (1985), Vol. 3, Chap. 9; d) P. P. Gaspar, D. Holten, and S. Konieczny, Acc. Chem. Res., 20, 329 (1987); e) Y.-N. Tang, "Reactive Intermediates, "ed by R. A. Abramovitch, Plenum Press, New York (1982), Vol. 2, Chap. 4; f) Y. Apeloig, "The Chemistry of Organic Silicon Compounds, "ed by S. Patai and Z. Rappoport, John Wiley, New York (1989), Part 1, Chap. 2; g) O. M. Nefedov, M. P. Egorov, A. I. Ioffe, L. G. Menchikov, P. S. Zuev, V. I. Minkin, B. Ya. Simkin, and M. N. Glukhovtsev, Pure Appl. Chem., 64, 265 (1992).
6. Reviews for silylenes, see: a) P. P. Gasper, "Reactive Intermediates," ed by M. Jones, Jr., and R. T. Moss, John Wiley, New York (1978), Vol. 1, Chap. 7; b) (1981), Vol. 2, Chap. 9; c) (1985), Vol. 3, Chap. 9; d) P. P. Gaspar, D. Holten, and S. Konieczny, Acc. Chem. Res., 20, 329 (1987); e) Y.-N. Tang, "Reactive Intermediates, "ed by R. A. Abramovitch, Plenum Press, New York (1982), Vol. 2, Chap. 4; f) Y. Apeloig, "The Chemistry of Organic Silicon Compounds, "ed by S. Patai and Z. Rappoport, John Wiley, New York (1989), Part 1, Chap. 2; g) O. M. Nefedov, M. P. Egorov, A. I. Ioffe, L. G. Menchikov, P. S. Zuev, V. I. Minkin, B. Ya. Simkin, and M. N. Glukhovtsev, Pure Appl. Chem., 64, 265 (1992).
7. Reviews for silylenes, see: a) P. P. Gasper, "Reactive Intermediates," ed by M. Jones, Jr., and R. T. Moss, John Wiley, New York (1978), Vol. 1, Chap. 7; b) (1981), Vol. 2, Chap. 9; c) (1985), Vol. 3, Chap. 9; d) P. P. Gaspar, D. Holten, and S. Konieczny, Acc. Chem. Res., 20, 329 (1987); e) Y.-N. Tang, "Reactive Intermediates, "ed by R. A. Abramovitch, Plenum Press, New York (1982), Vol. 2, Chap. 4; f) Y. Apeloig, "The Chemistry of Organic Silicon Compounds, "ed by S. Patai and Z. Rappoport, John Wiley, New York (1989), Part 1, Chap. 2; g) O. M. Nefedov, M. P. Egorov, A. I. Ioffe, L. G. Menchikov, P. S. Zuev, V. I. Minkin, B. Ya. Simkin, and M. N. Glukhovtsev, Pure Appl. Chem., 64, 265 (1992).
8. a) M. Karni and Y. Apeloig, J. Am. Chem. Soc., 112, 8584 (1900);
9. b) Y. Apeloig and T. Müller, J. Am. Chem. Soc., 117, 5363 (1995).
10. a) P. Foley and M. Zeldin, Inorg. Chem., 14, 2264 (1975);
11. b) P. J. Corvan and J. J. Zuckerman, Inorg. Chem. Acta, 34, L255 (1979);
12. c) M. M. Olmstead and P. P. Power, Inorg. Chem., 23, 413 (1984).
13. Cyclic dimer formation of fluorosilylenes has been proposed both theoretically and experimentally: a) P. Jutzi, U. Holtmann, H. Bögge, and A. Müller, J. Chem. Soc., Chem. Commun., 1988, 305; b) J. Maxka and Y. Apeloig, J. Chem. Soc., Chem. Commun., 1990, 737.
14. Cyclic dimer formation of fluorosilylenes has been proposed both theoretically and experimentally: a) P. Jutzi, U. Holtmann, H. Bögge, and A. Müller, J. Chem. Soc., Chem. Commun., 1988, 305; b) J. Maxka and Y. Apeloig, J. Chem. Soc., Chem. Commun., 1990, 737.
15. a) M. Denk, R. Lennon, R. Hayashi, R. West, A. V. Belyakov, H. P. Verne, A. Haaland, M. Wagner, and N. Metzler, J. Am.Chem. Soc., 116, 2691 (1994);
16. b) M. Denk, J. C. Green, N. Metzler, and M. Wagner, J. Chem. Soc., Dalton. Trans., 1994, 2405;
17. c) B. Gehrhus, M. F. Lappert, J. Heinicke, R. Boese, and D. Bläser, J. Chem. Soc., Chem. Commun., 1995, 1931.
18. a) F. Huppmann, W. Maringgele, T. Kottke, and A. Meller, J. Organomet. Chem., 434, 35 (1992);
19. b) F. Huppmann, M. Noltemeyer, and A. Meller, J. Organomet. Chem., 483, 217 (1994).
20. 9b, 10)
21. T. Hwang and C. Liu, J. Am. Chem. Soc., 102, 185 (1980).
22. a) N. Tokitoh, H. Suzuki, R. Okazaki, and K. Ogawa, J. Am. Chem. Soc., 116, 11572 (1994);
23. b) H. Suzuki, N. Tokitoh, and R. Okazaki, Bull. Chem. Soc. Jpn., 68, 2471 (1995).
24. N. Tokitoh, H. Suzuki, R. Okazaki, and K. Ogawa, J. Am. Chem. Soc., 115, 10428 (1993).
25. M. Ishikawa, M. Ishiguro, and M. Kumada, J. Organomet. Chem., 49, C71 (1973).
26. a) H. B. Yokelson, J. Maxka, D. A. Siegel, and R. West, J. Am. Chem. Soc., 108, 4239 (1986);
27. b) H. B. Yokelson, D. A. Siegel, A. J. Millevolte, J. Maxka, and R. West, Organometallics, 9, 1005 (1990).
28. 15b) The results show that the dissociation of usual alkyl-and aryldisilenes to the corresponding silylenes did not take place under the conditions. For a recent discussion on the disilene-silylene equilibrium, see: R. Okazaki and R. West, Adv. Organomet. Chem., 39, 231 (1996).
29. a) K. Krogh-Jespersen, J. Am. Chem. Soc., 107, 537 (1985);
30. b) R. S. Grev, H. F. Schaaefer, III, and K. M. Baines, J. Am. Chem. Soc., 112, 9458 (1990).
31. a) D. N. Roark and G. J. Peddle, J. Am. Chem. Soc., 94, 3837 (1972);
32. b) H. Sakurai, Y. Nakadaira, and T. Kobayashi, J. Am. Chem. Soc., 101, 487 (1979).
33. a) P. Boudjouk, U. Samaraweera, R. Sooriyakumaran, J. Chrusciel, and K. R. Anderson, Angew. Chem., Int. Ed. Engl., 27, 1355 (1988);
34. b) D. H. Pae, M. Xiao, M. Y. Chiang, and P. P. Gaspar, J. Am. Chem. Soc., 113, 1281 (1991);
35. c) M. Ishikawa, T. Horio, Y. Yuzuriha, A. Kunai, T. Tsukihara, and H. Naitou, Organometallics, 11, 597 (1992).
36. At the high temperatures, no amino-bridged silylene dimer would be formed. An initial adduct of silylene to benzene, a 7-silanorcaradiene, may be preferably cleaved to the corresponding silylene and benzene. 7,7-Dimethyl-7-silacyclohepta-1,3,5-triene is known to decompose to dimethylsilylene and benzene through the corresponding silanorcaradiene at 100 °C: Y. Nakadaira, R. Sato, and H. Sakurai, Organometallics, 10, 435 (1991).
37. R. Nagel and H. W. Post, J. Org. Chem., 17, 1379 (1952).
38. K. C. Frisch and R. B. Young, J. Am. Chem. Soc., 74, 4854 (1952).
39. D. J. Faulkner and L. E. Wolinsky, J. Org. Chem., 40, 389 (1975).
40. H. Breederveld and H. I. Waterman, Research, 7, S5 (1954); Chem. Abstr., 49, 2307b (1955).
41. H. Breederveld and H. I. Waterman, Research, 7, S5 (1954); Chem. Abstr., 49, 2307b (1955).