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

Zitieren

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, Nico, Kurscheid, Boris, Steinhauer, Simon, Neumann, Beate, Stammler, Hans-Georg, Ignat'ev, Nikolai, and Hoge, Berthold. 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.
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.

2 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Bis(perchlorocatecholato)silane-A Neutral Silicon Lewis Super Acid.
Maskey R, Schädler M, Legler C, Greb L., Angew Chem Int Ed Engl 57(6), 2018
PMID: 29240282
Pentafluoroethylated Compounds of Silicon, Germanium and Tin.
Wiesemann M, Hoge B., Chemistry 24(62), 2018
PMID: 29722451

34 References

Daten bereitgestellt von Europe PubMed Central.

Synthesis of chlorosilicates.
Steinhauer S, Bottcher T, Schwarze N, Neumann B, Stammler HG, Hoge B., Angew. Chem. Int. Ed. Engl. 53(48), 2014
PMID: 25256121

AUTHOR UNKNOWN, Angew. Chem. 126(), 2014

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Ignat'ev, J. Fluorine Chem. 171(), 2015

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Shevchenko, J. Fluorine Chem. 129(), 2008
Solid-state structure of a Li/F carbenoid: pentafluoroethyllithium.
Waerder B, Steinhauer S, Neumann B, Stammler HG, Mix A, Vishnevskiy YV, Hoge B, Mitzel NW., Angew. Chem. Int. Ed. Engl. 53(43), 2014
PMID: 25205058

AUTHOR UNKNOWN, Angew. Chem. 126(), 2014

AUTHOR UNKNOWN, 0
Synthesis of five- and six-coordinate tris(pentafluoroethyl)fluorosilicates.
Steinhauer S, Stammler HG, Neumann B, Ignat'ev N, Hoge B., Angew. Chem. Int. Ed. Engl. 53(2), 2013
PMID: 24288152

AUTHOR UNKNOWN, Angew. Chem. 126(), 2014

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0
Synthesis of tris- and tetrakis(pentafluoroethyl)silanes.
Steinhauer S, Bader J, Stammler HG, Ignat'ev N, Hoge B., Angew. Chem. Int. Ed. Engl. 53(20), 2014
PMID: 24692241

AUTHOR UNKNOWN, Angew. Chem. 126(), 2014

Thompson, J. Chem. Soc. (), 1929

AUTHOR UNKNOWN, 0

Narkon, Izvestiya Akademii Nauk SSSR Seriya Khimicheskaya 5(), 1979

Frohn, J. Organomet. Chem. 506(), 1996

Atoji, Acta Crystallogr. 7(), 1954

Zakharov, Eur. J. Inorg. Chem. (), 2013

Bent, Chem. Rev. 61(), 1961

AUTHOR UNKNOWN, 0

Kummer, J. Organomet. Chem. 178(), 1979
A short history of SHELX.
Sheldrick GM., Acta Crystallogr., A, Found. Crystallogr. 64(Pt 1), 2007
PMID: 18156677

Dolomanov, J. Appl. Crystallogr. 42(), 2009

Palatinus, J. Appl. Crystallogr. 40(), 2007
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