Synthesis of Functional Bis(pentafluoroethyl)silanes (C2F5)(2)SiX2, with X=H, F, Cl, Br, OPh, and O2CCF3

Schwarze N, Kurscheid B, Steinhauer S, Neumann B, Stammler H-G, Ignat'ev N, Hoge B (2016)
CHEMISTRY-A EUROPEAN JOURNAL 22(48): 17460-17467.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
As recently shown, the introduction of pentafluoroethyl functionalities into silicon compounds is of general interest due to an enhanced Lewis acidity of the resulting species. By this means, the synthesis of previously inaccessible hypervalent silicon derivatives is enabled. While an easy access to tris(pentafluoroethyl)silanes has already been published, synthetic strategies for the selective preparation of bis derivatives are yet unknown. In this contribution, a convenient protocol for the synthesis of functional bis(pentafluoroethyl)silicon compounds is presented. These compounds represent precursors for the synthesis of pentafluoroethylated polysiloxanes. Furthermore, they prove to be resistant to oxonium cations, which is a key feature for the preparation of stable pentafluoroethylsilic acids. Treatment of dichlorodiphenoxysilane with in situ generated pentafluoroethyl lithium leads to the corresponding bis(pentafluoroethyl)silane in high yields. (C2F5)(2)Si(OPh)(2) serves as a starting material for further functionalized bis(pentafluoroethyl)silanes. These silanes have been isolated and their reactivity towards N bases studied. The pronounced Lewis acidity of the obtained compounds has been documented by the formation of octahedral adducts with nitrogen donors such as 1,10-phenanthroline and acetonitrile.
Stichworte
fluorine; halogens; Lewis acids; perfluoroalkyl; silicon
Erscheinungsjahr
2016
Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
22
Ausgabe
48
Seite(n)
17460-17467
ISSN
0947-6539
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/2907428

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Schwarze N, Kurscheid B, Steinhauer S, et al. Synthesis of Functional Bis(pentafluoroethyl)silanes (C2F5)(2)SiX2, with X=H, F, Cl, Br, OPh, and O2CCF3. CHEMISTRY-A EUROPEAN JOURNAL. 2016;22(48):17460-17467.
Schwarze, N., Kurscheid, B., Steinhauer, S., Neumann, B., Stammler, H. - G., Ignat'ev, N., & Hoge, B. (2016). Synthesis of Functional Bis(pentafluoroethyl)silanes (C2F5)(2)SiX2, with X=H, F, Cl, Br, OPh, and O2CCF3. CHEMISTRY-A EUROPEAN JOURNAL, 22(48), 17460-17467. doi:10.1002/chem.201603442
Schwarze, N., Kurscheid, B., Steinhauer, S., Neumann, B., Stammler, H. - G., Ignat'ev, N., and Hoge, B. (2016). Synthesis of Functional Bis(pentafluoroethyl)silanes (C2F5)(2)SiX2, with X=H, F, Cl, Br, OPh, and O2CCF3. CHEMISTRY-A EUROPEAN JOURNAL 22, 17460-17467.
Schwarze, N., et al., 2016. Synthesis of Functional Bis(pentafluoroethyl)silanes (C2F5)(2)SiX2, with X=H, F, Cl, Br, OPh, and O2CCF3. CHEMISTRY-A EUROPEAN JOURNAL, 22(48), p 17460-17467.
N. Schwarze, et al., “Synthesis of Functional Bis(pentafluoroethyl)silanes (C2F5)(2)SiX2, with X=H, F, Cl, Br, OPh, and O2CCF3”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 22, 2016, pp. 17460-17467.
Schwarze, N., Kurscheid, B., Steinhauer, S., Neumann, B., Stammler, H.-G., Ignat'ev, N., Hoge, B.: Synthesis of Functional Bis(pentafluoroethyl)silanes (C2F5)(2)SiX2, with X=H, F, Cl, Br, OPh, and O2CCF3. CHEMISTRY-A EUROPEAN JOURNAL. 22, 17460-17467 (2016).
Schwarze, Nico, Kurscheid, Boris, Steinhauer, Simon, Neumann, Beate, Stammler, Hans-Georg, Ignat'ev, Nikolai, and Hoge, Berthold. “Synthesis of Functional Bis(pentafluoroethyl)silanes (C2F5)(2)SiX2, with X=H, F, Cl, Br, OPh, and O2CCF3”. CHEMISTRY-A EUROPEAN JOURNAL 22.48 (2016): 17460-17467.

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