Metal-free dehydrogenation of tri- and diethylamine with (C2F5)(3)PF2

Bader J, Neumann B, Stammler H-G, Ignat'ev N, Hoge B (2018)
JOURNAL OF FLUORINE CHEMISTRY 207: 12-17.

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Abstract / Notes
The reaction of the strong Lewis acid (C2F5)(3)PF2 with triethylamine leads to an initial hydride abstraction, resulting in the formation of the hydridophosphate anion [P(C2F5)(3)F2H](-) and the iminium ion [CH3CH = NEt2](+). The latter is deprotonated by a second molecule NEt3 which corresponds to a formal hydrogen abstraction from the amine. The resulting nucleophilic enamine is trapped by a second equivalent of (C2F5)(3)PF2, ultimately yielding the beta-aminovinylphosphorane derivative (C2F5)(2)PF2C2H2NEt2. The beta-aminovinylphosphorane reacts with CsF to the corresponding trifluorophosphate derivative, [P(C2F5)(2)F3C2H2NEt2](-), which hydrolyzes to the aldehyde [P(C2F5)(2)F3CH2CHO](-), while the reaction with anhydrous HF yields the zwitterionic species [P(C2F5)(2)F3C2H3NEt2].
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Bader J, Neumann B, Stammler H-G, Ignat'ev N, Hoge B. Metal-free dehydrogenation of tri- and diethylamine with (C2F5)(3)PF2. JOURNAL OF FLUORINE CHEMISTRY. 2018;207:12-17.
Bader, J., Neumann, B., Stammler, H. - G., Ignat'ev, N., & Hoge, B. (2018). Metal-free dehydrogenation of tri- and diethylamine with (C2F5)(3)PF2. JOURNAL OF FLUORINE CHEMISTRY, 207, 12-17. doi:10.1016/j.jfluchem.2017.12.015
Bader, J., Neumann, B., Stammler, H. - G., Ignat'ev, N., and Hoge, B. (2018). Metal-free dehydrogenation of tri- and diethylamine with (C2F5)(3)PF2. JOURNAL OF FLUORINE CHEMISTRY 207, 12-17.
Bader, J., et al., 2018. Metal-free dehydrogenation of tri- and diethylamine with (C2F5)(3)PF2. JOURNAL OF FLUORINE CHEMISTRY, 207, p 12-17.
J. Bader, et al., “Metal-free dehydrogenation of tri- and diethylamine with (C2F5)(3)PF2”, JOURNAL OF FLUORINE CHEMISTRY, vol. 207, 2018, pp. 12-17.
Bader, J., Neumann, B., Stammler, H.-G., Ignat'ev, N., Hoge, B.: Metal-free dehydrogenation of tri- and diethylamine with (C2F5)(3)PF2. JOURNAL OF FLUORINE CHEMISTRY. 207, 12-17 (2018).
Bader, Julia, Neumann, Beate, Stammler, Hans-Georg, Ignat'ev, Nikolai, and Hoge, Berthold. “Metal-free dehydrogenation of tri- and diethylamine with (C2F5)(3)PF2”. JOURNAL OF FLUORINE CHEMISTRY 207 (2018): 12-17.
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