Synthesis and Reactivity of New Functionalized Perfluoroalkylfluorophosphates
Allefeld N, Neumann B, Stammler H-G, Roeschenthaler G-V, Ignat'ev N, Hoge B (2014)
Chemistry - A European Journal 20(25): 7736-7745.
Zeitschriftenaufsatz
| Veröffentlicht | Englisch
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Autor*in
Allefeld, NadineUniBi;
Neumann, BeateUniBi;
Stammler, Hans-GeorgUniBi;
Roeschenthaler, Gerd-Volker;
Ignat'ev, Nikolai;
Hoge, BertholdUniBi
Einrichtung
Abstract / Bemerkung
A new efficient synthesis of functionalized perfluoroalkyl fluorophosphates by oxidative addition of Me2NCH2F to the electron-deficient phosphanes (C2F5)(n)PF3-n (n = 0-3) is reported. The initially formed zwitterionic, hexa-coordinated phosphates [(C2F5)(n)F5-nP(CH2NMe2-CH2NMe2)] are converted into the corresponding phosphonium salts [(Me3PCH2NMe2](+)[(C2F5)(n)F5-nP(CH2NMe2)](-) by treatment with PMe3. In addition [(C2F5)(3)F2P(CH2NMe2-CH2NMe2)] can undergo a 1,3-methyl shift from the internal to the terminal nitrogen-a structural characterization was achieved from the CF3 analogue. Reaction of [(C2F5)(3)F2P(CH2NMe-CH2NMe3)] and PMe3 gave rise to the formation of the zwitterionic phosphonium phosphate [(C2F5)(3)F2P(CH2NMe-CH2PMe3)], which was fully characterized by X-ray diffraction analysis. Moreover, an efficient one-pot synthesis of Cs+ [(C2F5)(3)F2P(CH2NMe2)](-) was pursued. This salt turned out to be a useful nucleophile in several alkylation reactions.
Stichworte
fluorine;
phosphorus;
phosphate;
iminium;
oxidative addition
Erscheinungsjahr
2014
Zeitschriftentitel
Chemistry - A European Journal
Band
20
Ausgabe
25
Seite(n)
7736-7745
ISSN
0947-6539
Page URI
https://pub.uni-bielefeld.de/record/2685845
Zitieren
Allefeld N, Neumann B, Stammler H-G, Roeschenthaler G-V, Ignat'ev N, Hoge B. Synthesis and Reactivity of New Functionalized Perfluoroalkylfluorophosphates. Chemistry - A European Journal. 2014;20(25):7736-7745.
Allefeld, N., Neumann, B., Stammler, H. - G., Roeschenthaler, G. - V., Ignat'ev, N., & Hoge, B. (2014). Synthesis and Reactivity of New Functionalized Perfluoroalkylfluorophosphates. Chemistry - A European Journal, 20(25), 7736-7745. doi:10.1002/chem.201402421
Allefeld, Nadine, Neumann, Beate, Stammler, Hans-Georg, Roeschenthaler, Gerd-Volker, Ignat'ev, Nikolai, and Hoge, Berthold. 2014. “Synthesis and Reactivity of New Functionalized Perfluoroalkylfluorophosphates”. Chemistry - A European Journal 20 (25): 7736-7745.
Allefeld, N., Neumann, B., Stammler, H. - G., Roeschenthaler, G. - V., Ignat'ev, N., and Hoge, B. (2014). Synthesis and Reactivity of New Functionalized Perfluoroalkylfluorophosphates. Chemistry - A European Journal 20, 7736-7745.
Allefeld, N., et al., 2014. Synthesis and Reactivity of New Functionalized Perfluoroalkylfluorophosphates. Chemistry - A European Journal, 20(25), p 7736-7745.
N. Allefeld, et al., “Synthesis and Reactivity of New Functionalized Perfluoroalkylfluorophosphates”, Chemistry - A European Journal, vol. 20, 2014, pp. 7736-7745.
Allefeld, N., Neumann, B., Stammler, H.-G., Roeschenthaler, G.-V., Ignat'ev, N., Hoge, B.: Synthesis and Reactivity of New Functionalized Perfluoroalkylfluorophosphates. Chemistry - A European Journal. 20, 7736-7745 (2014).
Allefeld, Nadine, Neumann, Beate, Stammler, Hans-Georg, Roeschenthaler, Gerd-Volker, Ignat'ev, Nikolai, and Hoge, Berthold. “Synthesis and Reactivity of New Functionalized Perfluoroalkylfluorophosphates”. Chemistry - A European Journal 20.25 (2014): 7736-7745.
41 References
Daten bereitgestellt von Europe PubMed Central.
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
Swatloski, Green Chem. 5(), 2003
Plakhotnyk, J. Fluorine Chem. 126(), 2005
Ponikvar, J. Fluorine Chem. 123(), 2003
AUTHOR UNKNOWN, 0
Schmidt, J. Power Sources 97-98(), 2001
AUTHOR UNKNOWN, 0
Lithium-ion conducting electrolyte salts for lithium batteries.
Aravindan V, Gnanaraj J, Madhavi S, Liu HK., Chemistry 17(51), 2011
PMID: 22114046
Aravindan V, Gnanaraj J, Madhavi S, Liu HK., Chemistry 17(51), 2011
PMID: 22114046
Xie, J. Phys. Chem. C 115(), 2011
González, Tribol. Lett. 40(), 2010
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
Ignat’ev, J. Fluorine Chem. 103(), 2000
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
Komkov, Z. Obshchei Khim. 32(), 1962
Schmutzler, Chem. Ind. (), 1962
Schmutzler, Inorg. Chem. 3(), 1964
AUTHOR UNKNOWN, 0
Nixon, J. Inorg. Nucl. Chem. 31(), 1969
Kolomeitsev, J. Fluorine Chem. 71(), 1995
Görg, J. Fluorine Chem. 79(), 1996
Böttcher, Organometallics 31(), 2012
[Alpha-halogenic amines. XXIV. Preparation and properties of fluoromethyldialkylamines]
Bohme H, Hilp M., Chem. Ber. 103(1), 1970
PMID: 5410741
Bohme H, Hilp M., Chem. Ber. 103(1), 1970
PMID: 5410741
Igumnov, Russ. Chem. Bull. 30(), 1981
Christe, J. Am. Chem. Soc. 116(), 1994
Böhme, Justus Liebigs Ann. Chem. 705(), 1967
Ignat′ev, J. Fluorine Chem. 126(), 2005
Lundberg, Inorg. Chem. 8(), 1969
Clark, J. Chem. Soc. Faraday Trans. 90(), 1994
Mahjoub, Z. Anorg. Allg. Chem. 618(), 1992
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
Zakharov, Eur. J. Inorg. Chem. (), 2013
AUTHOR UNKNOWN, 0
Dolomanov, J. Appl. Crystallogr. 42(), 2009
A short history of SHELX.
Sheldrick GM., Acta Crystallogr., A, Found. Crystallogr. 64(Pt 1), 2007
PMID: 18156677
Sheldrick GM., Acta Crystallogr., A, Found. Crystallogr. 64(Pt 1), 2007
PMID: 18156677
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