Decamethylsilicocene chemistry: Reaction with representative aldehydes and ketones

Jutzi P, Eikenberg D, Bunte EA, Mohrke A, Neumann B, Stammler H-G (1996)
ORGANOMETALLICS 15(7): 1930-1934.

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Abstract
Reactions of decamethylsilicocene, (Me(5)C(5))(2)Si (1), with representative organic carbonyl compounds are described. They proceed via [2 + 1] cycloaddition products of the oxasilirane type as reactive intermediates to give different types of compounds. The formal oxidation state of silicon is changed from +II in the substrate to +IV in the final products; at the same time the hapticity of the pentamethylcyclopentadienyl ligands changes from eta(5) to eta(1). In the reaction of 1 with aldehydes such as benzaldehyde and trans-cinnamaldehyde as well as with acetone, formation of the respective dioxasilolane derivatives 2, 3, and 5 takes place. Here, C-C bond formation is observed for the first time in the reaction of a divalent silicon compound; reaction with the aldehydes is stereospecific. In the reaction of 1 with acetophenone or benzophenone, the bicyclic ring systems 6 and 7, respectively, containing an oxasilacyclopentene unit are formed by rearrangement of the transient oxasiliranes, The 1,3,2-dioxasilole 9 is the product of the reaction of 1 with benzil. The new compounds are characterized by NMR (H-1, C-13, Si-29) spectroscopy and by mass spectrometry and microanalytical data. The X-ray crystal structure analysis of 2 is presented.
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Jutzi P, Eikenberg D, Bunte EA, Mohrke A, Neumann B, Stammler H-G. Decamethylsilicocene chemistry: Reaction with representative aldehydes and ketones. ORGANOMETALLICS. 1996;15(7):1930-1934.
Jutzi, P., Eikenberg, D., Bunte, E. A., Mohrke, A., Neumann, B., & Stammler, H. - G. (1996). Decamethylsilicocene chemistry: Reaction with representative aldehydes and ketones. ORGANOMETALLICS, 15(7), 1930-1934.
Jutzi, P., Eikenberg, D., Bunte, E. A., Mohrke, A., Neumann, B., and Stammler, H. - G. (1996). Decamethylsilicocene chemistry: Reaction with representative aldehydes and ketones. ORGANOMETALLICS 15, 1930-1934.
Jutzi, P., et al., 1996. Decamethylsilicocene chemistry: Reaction with representative aldehydes and ketones. ORGANOMETALLICS, 15(7), p 1930-1934.
P. Jutzi, et al., “Decamethylsilicocene chemistry: Reaction with representative aldehydes and ketones”, ORGANOMETALLICS, vol. 15, 1996, pp. 1930-1934.
Jutzi, P., Eikenberg, D., Bunte, E.A., Mohrke, A., Neumann, B., Stammler, H.-G.: Decamethylsilicocene chemistry: Reaction with representative aldehydes and ketones. ORGANOMETALLICS. 15, 1930-1934 (1996).
Jutzi, Peter, Eikenberg, D, Bunte, EA, Mohrke, A, Neumann, B, and Stammler, Hans-Georg. “Decamethylsilicocene chemistry: Reaction with representative aldehydes and ketones”. ORGANOMETALLICS 15.7 (1996): 1930-1934.
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