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.

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Abstract
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.
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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.
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.
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