Chemistry of decamethylsilicocene: Oxidative addition of compounds with X-H bonds (X = F, Cl, Br, O, S)

Jutzi P, Bunte E-A, Holtmann U, Neumann B, Stammler H-G (1993)
Journal of Organometallic Chemistry 446(1-2): 139-147.

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Abstract
In the reaction of decamethylsilicocene (1) with protic substrates HX, the corresponding oxidative addition products 2–9, 11, 12, and 15 of the type ([sigma]-Me5C5)2Si(H)X are formed in good yields. Reactions of the hydrogen halides HF, HCl, and HBr with 1 lead to the silanes 2, 3 and 4, respectively. The oxo acids trifluoroacetic acid and propionic acid react with 1 to give the compounds 5 and 6, respectively. Phenol and p-methylphenol add to 1 to give the compounds 7 and 8, respectively. In the reaction of 4-methyl-catechol with 1, the oxidative addition product 9 is an intermediate; 9 decomposes with catalytic amounts of water or pyridine to give the o-phenylenedioxysilane 10a. Compound 10b is obtained from 1 and catechol. Treatment of 1 with cyclohexanone-oxime and ethanal-oxime leads to the addition products 11 and 12, respectively. The six-membered heterocycles 13 and 14 are formed in the reaction of 1 with the corresponding 1,3-diketones. Oxidative addition products are postulated as intermediates; they rearrange by Cp* migration and Si-O bond formation. The silane 15 is obtained from the reaction of 1 with p-methyl-phenylthiol. The new compounds have been characterized by NMR, IR, and mass spectrometry, and in the case of 9, 10b, and 13 by an X-ray crystal structure determination as well. The mechanism of the oxidative addition processes is discussed.
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Jutzi P, Bunte E-A, Holtmann U, Neumann B, Stammler H-G. Chemistry of decamethylsilicocene: Oxidative addition of compounds with X-H bonds (X = F, Cl, Br, O, S). Journal of Organometallic Chemistry. 1993;446(1-2):139-147.
Jutzi, P., Bunte, E. - A., Holtmann, U., Neumann, B., & Stammler, H. - G. (1993). Chemistry of decamethylsilicocene: Oxidative addition of compounds with X-H bonds (X = F, Cl, Br, O, S). Journal of Organometallic Chemistry, 446(1-2), 139-147.
Jutzi, P., Bunte, E. - A., Holtmann, U., Neumann, B., and Stammler, H. - G. (1993). Chemistry of decamethylsilicocene: Oxidative addition of compounds with X-H bonds (X = F, Cl, Br, O, S). Journal of Organometallic Chemistry 446, 139-147.
Jutzi, P., et al., 1993. Chemistry of decamethylsilicocene: Oxidative addition of compounds with X-H bonds (X = F, Cl, Br, O, S). Journal of Organometallic Chemistry, 446(1-2), p 139-147.
P. Jutzi, et al., “Chemistry of decamethylsilicocene: Oxidative addition of compounds with X-H bonds (X = F, Cl, Br, O, S)”, Journal of Organometallic Chemistry, vol. 446, 1993, pp. 139-147.
Jutzi, P., Bunte, E.-A., Holtmann, U., Neumann, B., Stammler, H.-G.: Chemistry of decamethylsilicocene: Oxidative addition of compounds with X-H bonds (X = F, Cl, Br, O, S). Journal of Organometallic Chemistry. 446, 139-147 (1993).
Jutzi, Peter, Bunte, Ernst-August, Holtmann, Udo, Neumann, Beate, and Stammler, Hans-Georg. “Chemistry of decamethylsilicocene: Oxidative addition of compounds with X-H bonds (X = F, Cl, Br, O, S)”. Journal of Organometallic Chemistry 446.1-2 (1993): 139-147.
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