Abstract
The hydrosilylation reactions of allylgermanes R3GeAll (R3 = Cl3, Me3) in the presence of a platinum catalyst (Karstedt catalyst) with methylchlorohydridesilanes MenCl3–nSiH (n = 0–2) and 1,1,3,3-tetramethyldisiloxane have been studied. It was found that only 1,3-adducts are formed. In some cases, the replacement of only one methyl group at silicon with Cl (or vice versa, Cl for methyl group) leads not only to a decrease in the yields of the products obtained, but to a complete absence of reaction. A possible route of the studied reactions is proposed. The identification of the synthesized compounds was carried out using the methods of gas-liquid chromatography, 1H NMR spectroscopy and chromatography-mass spectrometry.
Similar content being viewed by others
REFERENCES
Sheludyakov, V.D., Zhun’, V.I., Vlasenko, S.D., Bochkarev, V.N., Slyusarenko, T.F., Kisin, A.V., Nosova, V.M., Turkel’taub, G.N., and Chernyshev, E.A., Zh. Obshch. Khim., 1981, vol. 51, no. 9, p. 2022.
Zhun’, V.I., Zhun’, A.B., Vlasenko, S.D., Belorusskaya, L.A., Chernyshev, E.A., and Sheludyakov, V.D., Zh. Obshch. Khim., 1982, vol. 52, no. 11, p. 2065.
Vlasenko, S.D., Candidate Sci. (Chem.) Dissertation, Moscow, 1983.
Chernyshev, E.A., Belyakova, Z.V., Knyazev, S.P., Shherbakova, T.V., and Kuznetsov, V.M., Vestn. MITKhT, 2008, vol. 5, no. 1, p. 27.
Marciniec, B., Comprehensive Handbook on Hydrosilylation, Oxford: Pergamon Press, 1992, p. 754.
Zhun’, V.I., Tsvetkov, A.L., Bochkarev, V.N., Slyusarenko, T.F., Turkel’taub, G.N., and Sheludyakov, V.D., Zh. Obshch. Khim., 1989, vol. 59, no. 2, p. 390.
Parshkova, L.A., Candidate Sci. (Chem.) Dissertation, Moscow, 2015.
Franczyk, A., Stefanowska, K., Dutkiewicz, M., Frąckowiak, D., and Marciniec, B., Dalton Trans., 2017, vol. 46, no. 1, p. 158. https://doi.org/10.1039/c6dt04190f
Walczak, M., Stefanowska, K., Franczyk, A., Walkowiak, J., Wawrzyńczak, A., and Marciniec, B., J. Catal., 2018, vol. 367, p. 1. https://doi.org/10.1016/j.jcat.2018.08.012
Walczak, M., Januszewski, R., Franczyk, A., and Marciniec, B., J. Organomet. Chem., 2018, vol. 872, p. 73. https://doi.org/10.1016/j.jorganchem.2018.07.021
Walczak, M., Franczyk, A., Dutkiewicz, M., and Marciniec, B., Organometallics, 2019, vol. 38, p. 3018. https://doi.org/10.1021/acs.organomet.9b00350
Kaźmierczak, J., Kuciński, K., Szudkowska-Frątczak, J., and Hreczycho, G., Eur. J. Inorg. Chem., 2017, vol. 13, p. 1888. https://doi.org/10.1002/ejic.20170008
Grzelak, M., Frąckowiak, D., Januszewski, R., and Marciniec, B., Dalton Trans., 2020, vol. 49, no. 16, p. 5050. https://doi.org/10.1039/D0DT00557F
Nédez, C., Choplin, A., Basset, J.M., and Benazzi, E., Inorg. Chem., 1994, vol. 33, no. 6, p. 1094. https://doi.org/10.1021/ic00084a020
Schmidbauer, H. and Rott, J., Z. Naturforsch. B, 1990, vol. 45, p. 961. https://doi.org/10.1515/znb-1990-0708
Kocher, J., Lehnig, M., and Neumann, W.P., Organometallics, 1988, vol. 7, no. 5, p. 1201. https://doi.org/10.1021/om00095a029
Zaikin, V.G., Varlamov, A.V., Mikaya, A.I., and Prostakov, N.S., Osnovy mass-spektrometrii organicheskikh soedinenii (Basics of Mass Spectrometry of Organic Compounds), Moscow: MAIK, Nauka/Interperiodika, 2001, p. 286.
Terent’ev, P.B., Mass-spektrometriya v organicheskoi khimii (Mass Spectrometry in Organic Chemistry), Moscow: Vysshaya Shkola, 1979, p. 223.
Smirnov, B.M., Cluster Ions and Van der Waals Molecules, Philadelphia: Gordon and Breach, 1992.
Chalk, A.J. and Harrod, J.F., J. Am. Chem. Soc., 1965, vol. 87, no. 1, p. 21. https://doi.org/10.1021/ja01079a005
Deleris, G., Pillot, J.P., and Rayex, J.G., Tetrahedron, 1980, vol. 36, no. 15, p. 2215. https://doi.org/10.1016/0040-4020(80)80114-1
Lebr, M., Mazerol’, P., and Satzhe, J., Organic Compounds of Germanium, Moscow: Мир, 1974, p. 154.
NIST 11. NIST/EPA/NIH (NIST 11) Mass Spectral Data base., 2011.
Nametkin, N.S., Korolev, V.K., and Kuz’min, O.V., Dokl. Akad. Nauk SSSR, 1972, vol. 205, no. 5, p. 1111.
Petrov, A.D., Mironov, V.F., and Dolgii, I.E., Izv. Akad. Nauk SSSR, Ser. Khim., 1956, no. 9, p. 1146.
Mironov, V.F., Gar, T.K., and Buyakov, A.A., Zh. Obshch. Khim., 1973, vol. 43, no. 4, p. 798.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Rights and permissions
About this article
Cite this article
Lakhtin, V.G., Efimenko, D.A., Filippov, A.M. et al. Hydrosilylation of Allylgermanes. Russ J Gen Chem 91, 77–84 (2021). https://doi.org/10.1134/S1070363221010084
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363221010084