Reactions of a spiro trisilane with palladium complexes: Synthesis and structure of tris(organosilyl)CpPdIV and Bis(organosilyl)(μ-organosilylene)PdII2 complexes

Organometallics

Volumn 17, Issue 4, 1998, Pages 495-497

  Suginome, Michinori ^a   Kato, Yukitoshi ^a   Takeda, Nobuhiko ^a   Oike, Hideaki ^a   Ito, Yoshihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001471944     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9710778     Document Type: Article

References (25)

1. (a) Horn, K. A. Chem. Rev. (Washington, D.C.) 1995, 95, 1317-1350.
2. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. (Washington, D.C.) 1995, 95, 1351-1374.
3. (a) Suginome, M.; Oike, H.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 1665-1666.
4. (b) Suginome, M.; Oike, H.; Shuff, P. H.; Ito, Y. Organometallics 1996, 15, 2170-2178.
5. For cyclodimerization, see: (a) Tamao, K.; Hayashi, T.; Kumada, M. J. Organomet. Chem. 1976, 114, C19-21. (b) Kusukawa, T.; Kabe, Y.; Ando, W. Chem. Lett. 1993, 985-988. (c) Kusukawa, T.; Kabe, Y.; Nestler, B.; Ando, W. Organometallics 1995, 14, 2556-2564. For polymerization, see: (d) Suzuki, M.; Obayashi, T.; Amii, H.; Saegusa, T. Polym. Prepr. Jpn. 1991, 40, 355. (e) Uchimaru, Y.; Tanaka, Y.; Tanaka, M. Chem. Lett. 1995, 164.
6. For cyclodimerization, see: (a) Tamao, K.; Hayashi, T.; Kumada, M. J. Organomet. Chem. 1976, 114, C19-21. (b) Kusukawa, T.; Kabe, Y.; Ando, W. Chem. Lett. 1993, 985-988. (c) Kusukawa, T.; Kabe, Y.; Nestler, B.; Ando, W. Organometallics 1995, 14, 2556-2564. For polymerization, see: (d) Suzuki, M.; Obayashi, T.; Amii, H.; Saegusa, T. Polym. Prepr. Jpn. 1991, 40, 355. (e) Uchimaru, Y.; Tanaka, Y.; Tanaka, M. Chem. Lett. 1995, 164.
7. For cyclodimerization, see: (a) Tamao, K.; Hayashi, T.; Kumada, M. J. Organomet. Chem. 1976, 114, C19-21. (b) Kusukawa, T.; Kabe, Y.; Ando, W. Chem. Lett. 1993, 985-988. (c) Kusukawa, T.; Kabe, Y.; Nestler, B.; Ando, W. Organometallics 1995, 14, 2556-2564. For polymerization, see: (d) Suzuki, M.; Obayashi, T.; Amii, H.; Saegusa, T. Polym. Prepr. Jpn. 1991, 40, 355. (e) Uchimaru, Y.; Tanaka, Y.; Tanaka, M. Chem. Lett. 1995, 164.
8. For cyclodimerization, see: (a) Tamao, K.; Hayashi, T.; Kumada, M. J. Organomet. Chem. 1976, 114, C19-21. (b) Kusukawa, T.; Kabe, Y.; Ando, W. Chem. Lett. 1993, 985-988. (c) Kusukawa, T.; Kabe, Y.; Nestler, B.; Ando, W. Organometallics 1995, 14, 2556-2564. For polymerization, see: (d) Suzuki, M.; Obayashi, T.; Amii, H.; Saegusa, T. Polym. Prepr. Jpn. 1991, 40, 355. (e) Uchimaru, Y.; Tanaka, Y.; Tanaka, M. Chem. Lett. 1995, 164.
9. For cyclodimerization, see: (a) Tamao, K.; Hayashi, T.; Kumada, M. J. Organomet. Chem. 1976, 114, C19-21. (b) Kusukawa, T.; Kabe, Y.; Ando, W. Chem. Lett. 1993, 985-988. (c) Kusukawa, T.; Kabe, Y.; Nestler, B.; Ando, W. Organometallics 1995, 14, 2556-2564. For polymerization, see: (d) Suzuki, M.; Obayashi, T.; Amii, H.; Saegusa, T. Polym. Prepr. Jpn. 1991, 40, 355. (e) Uchimaru, Y.; Tanaka, Y.; Tanaka, M. Chem. Lett. 1995, 164.
10. The high reactivity of 1 was pointed out in palladium-catalyzed bis-silylation reactions, see: (a) Sakurai, H.; Kamiyama, Y.; Nakadaira, Y. J. Am. Chem. Soc. 1975, 97, 931-932. (b) Sakurai, H.; Kamiyama, Y.; Nakadaira, Y. Chem. Lett. 1975, 887-890.
11. The high reactivity of 1 was pointed out in palladium-catalyzed bis-silylation reactions, see: (a) Sakurai, H.; Kamiyama, Y.; Nakadaira, Y. J. Am. Chem. Soc. 1975, 97, 931-932. (b) Sakurai, H.; Kamiyama, Y.; Nakadaira, Y. Chem. Lett. 1975, 887-890.
12. 3: C, 52.55; H, 10.58. Found: C, 52.54; H, 10.74.
13. For palladium-isonitrile-catalyzed bis-silylations of alkenes and alkynes, see: (a) Suginome, M.; Matsumoto, A.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3061-3062. (b) Suginome, M.; Iwanami, T.; Matsumoto, A.; Ito, Y. Tetrahedron: Asymmetry 1997, 8, 859-862 and references therein.
14. For palladium-isonitrile-catalyzed bis-silylations of alkenes and alkynes, see: (a) Suginome, M.; Matsumoto, A.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3061-3062. (b) Suginome, M.; Iwanami, T.; Matsumoto, A.; Ito, Y. Tetrahedron: Asymmetry 1997, 8, 859-862 and references therein.
15. Suginome, M.; Oike, H.; Park, S.-S.; Ito, Y. Bull. Chem. Soc. Jpn. 1996, 69, 289-299.
16. w = 0.097.
17. Maitlis, P. M.; Espinet, P.; Russel, M. J. H. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon: Oxford, 1982; Vol. 6, pp 233-242.
18. 3: C, 49.01; H, 7.71. Found: C, 48.74: H, 7.89.
19. (a) Recently, a six-coordinated bis(phosphine)tetrakis(organosilyl)palladium(IV) complex was reported, see: Shimada, S.; Tanaka, M.; Shiro, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1856-1858. For alkyl derivatives of palladium(IV) complexes, see: (b) Canty, A. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Puddephatt, R. J., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, pp 225-290. Canty, A. J.; Jin, H.; Roberts, A. S.; Skelton, B. W.; White, A. H. Organometallics 1996, 15, 5713-5722.
20. (a) Recently, a six-coordinated bis(phosphine)tetrakis(organosilyl)palladium(IV) complex was reported, see: Shimada, S.; Tanaka, M.; Shiro, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1856-1858. For alkyl derivatives of palladium(IV) complexes, see: (b) Canty, A. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Puddephatt, R. J., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, pp 225-290. Canty, A. J.; Jin, H.; Roberts, A. S.; Skelton, B. W.; White, A. H. Organometallics 1996, 15, 5713-5722.
21. (a) Recently, a six-coordinated bis(phosphine)tetrakis(organosilyl)palladium(IV) complex was reported, see: Shimada, S.; Tanaka, M.; Shiro, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1856-1858. For alkyl derivatives of palladium(IV) complexes, see: (b) Canty, A. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Puddephatt, R. J., Eds.; Pergamon Press: Oxford, 1995; Vol. 9, pp 225-290. Canty, A. J.; Jin, H.; Roberts, A. S.; Skelton, B. W.; White, A. H. Organometallics 1996, 15, 5713-5722.
22. w = 0.088.
23. (a) Pan, Y.; Mague, J. T.; Fink, M. J. Organometallics 1992, 11, 3495-3497.
24. (b) Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900-2902.
25. The mechanism of the "back biting" may involve intramolecular metathesis of the Pd-Si and Si-Si bonds as outlined in the following equation. (Equation Presented)