Metal-free dehydrogenation of tri- and diethylamine with (C<sub>2</sub>F<sub>5</sub>)<sub>3</sub>PF<sub>2</sub>

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

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
Download
Es wurde kein Volltext hochgeladen. Nur Publikationsnachweis!
Abstract / Bemerkung
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].
Stichworte
Hydride abstraction; Phosphate; Pentafluoroethyl; Fluorine; Amines
Erscheinungsjahr
2018
Zeitschriftentitel
JOURNAL OF FLUORINE CHEMISTRY
Band
207
Seite(n)
12-17
ISSN
0022-1139
eISSN
1873-3328
Page URI
https://pub.uni-bielefeld.de/record/2918654

Zitieren

Bader J, Neumann B, Stammler H-G, Ignat'ev N, Hoge B. Metal-free dehydrogenation of tri- and diethylamine with (C<sub>2</sub>F<sub>5</sub>)<sub>3</sub>PF<sub>2</sub>. 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 (C<sub>2</sub>F<sub>5</sub>)<sub>3</sub>PF<sub>2</sub>. 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 (C<sub>2</sub>F<sub>5</sub>)<sub>3</sub>PF<sub>2</sub>. JOURNAL OF FLUORINE CHEMISTRY 207, 12-17.
Bader, J., et al., 2018. Metal-free dehydrogenation of tri- and diethylamine with (C<sub>2</sub>F<sub>5</sub>)<sub>3</sub>PF<sub>2</sub>. JOURNAL OF FLUORINE CHEMISTRY, 207, p 12-17.
J. Bader, et al., “Metal-free dehydrogenation of tri- and diethylamine with (C<sub>2</sub>F<sub>5</sub>)<sub>3</sub>PF<sub>2</sub>”, 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 (C<sub>2</sub>F<sub>5</sub>)<sub>3</sub>PF<sub>2</sub>. 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 (C<sub>2</sub>F<sub>5</sub>)<sub>3</sub>PF<sub>2</sub>”. JOURNAL OF FLUORINE CHEMISTRY 207 (2018): 12-17.