Silicon-carbon unsaturated compounds. 55. Synthesis and reactions of lithium silenolates, silicon analogs of lithium enolates

Organometallics

Volumn 15, Issue 14, 1996, Pages 3136-3146

  Ohshita, Joji ^a   Masaoka, Shin ^a   Masaoka, Yoshiteru ^a   Hasebe, Hidenobu ^a   Ishikawa, Mitsuo ^a   Tachibana, Akitomo ^b   Yano, Tasuku ^b   Yamabe, Tokio ^b  

^a HIROSHIMA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001315965     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950898e     Document Type: Article

References (24)

1. (a) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988.
2. (b) Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: New York, 1983.
3. For review, see: Caine, D. In Comprehensive Organonic Synthesis; Pergamon Press: Oxford, U.K., Vol. 3, Chapter 1.1, 1991.
4. (a) Ohshita, J.; Masaoka, Y.; Ishikawa, M. Organometallics 1991, 10, 3775.
5. (b) Ohshita, J.; Masaoka, Y.; Ishikawa, M.; Takeuchi, T. Organometallics 1993, 12, 876. For related work, see also ref 5.
6. Biltueva I. S.; Bravo-Zhivotovskii, D. A.; Kalikhman, I. D.; Vitkovskii, V. Yu; Shevchenko, S. G.; Vyazankin. N. S.; Voronkov, M. G. J. Organomet. Chem. 1989, 368, 163.
7. (a) Brook A. G.; Chiu, P.; McClenaghnan, J.; Lough, A. J. Organometallics 1991, 10, 3292.
8. (b) Bravo-Zhivotovskii, D.; Braude, V.; Stanger, A.; Kapon, M.; Apeloig, Y. Organometallics 1992, 11, 2326.
9. (c) Krempner, C.; Oehme, H. J. Organomet. Chem. 1994, 464, C7.
10. (d) Krempner, C.; Reinke, H.; Oehme, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1615.
11. Brook, A. G.; Nyburg, S. C.; Abdesaken, F.; Gutekunst, B.; Gutekunst, G.; Krishna, R.; Kallury, M. R.; Poon, Y. C.; Chang, Y.-M.; Wong-Ng, W. J. Am. Chem. Soc. 1982, 104, 5667.
12. Ohshita, J.; Masaoka, Y.; Masaoka, S.; Ishikawa, M.; Tachibana, A.; Yano, T.; Yamabe, T. J. Organomet. Chem. 1994, 473, 15.
13. Bravo-Zhivotovskii, D.; Apeloig, Y.; Ovchinnikov, Y.; Igonin, V.; Struchkov, Y. T. J. Organomet. Chem. 1993, 446, 123.
14. Brook, A. G.; Wessely, H.-J. Organometallics 1985, 4, 1487.
15. Thermal equilibrium between acylpolysilanes and siloxysilenes has been reported previously. See: (a) Brook, A. G.; Harris, J. W.; Lennon, J.; El Sheikh, M.; J. Am. Chem. Soc. 1979, 101, 83. (b) Ohshita, J.; Hasebe, H.; Masaoka, Y. Ishikawa, M. Organometallics 1994, 13, 1064.
16. Thermal equilibrium between acylpolysilanes and siloxysilenes has been reported previously. See: (a) Brook, A. G.; Harris, J. W.; Lennon, J.; El Sheikh, M.; J. Am. Chem. Soc. 1979, 101, 83. (b) Ohshita, J.; Hasebe, H.; Masaoka, Y. Ishikawa, M. Organometallics 1994, 13, 1064.
17. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1992.
18. 3SiLi. We have attempted to obtain optimized geometries of the products in the presence of the lithium cation, by using ab initio calculations, but have not yet succeeded. Therefore, we have omitted the lithium cation from the present calculations. Our attempts to find transition states of the reactions in the presence of the lithium cation by ab initio calculations have been also unsuccessful. They may be performed by using significantly more computing time and will be reported in the future.
19. Brook, A. G.; Nyburg, S. C.; Abdesaben, F.; Gutekunst, B.; Gutekunst, G.; Kallury, R. K. M. R.; Poon, Y. C.; Chang, Y.-M.; Wong-Ng, W. J. Am. Chem. Soc. 1982, 104, 5667.
20. Gutekunst, G.; Brook, A. G. J. Organomet. Chem. 1982, 225, 1.
21. Gilman, H.; Lichtenwalter, G. D. J. Am. Chem. Soc. 1958, 80, 608.
22. Gilman, H.; Smith, C. L. J. Am. Chem. Soc. 1964, 86, 1454.
23. Gilman, H.; Holmes, J. M.; Smith, C. L. Chem, Ind. 1965, 848.
24. Baines, K. M.; Brook, A. G. Organometallics 1987, 6, 692.