Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium

Waerder B, Steinhauer S, Neumann B, Stammler H-G, Mix A, Vishnevskiy Y, Hoge B, Mitzel NW (2014)
Angewandte Chemie International Edition 53(43): 11640-11644.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
Lithium carbenoids are versatile compounds for synthesis owing to their intriguing ambiphilic behavior. Although this class of compounds has been known for several years, few solid-state structures exist because of their high reactivity and often low thermal stability. Using cryo X-ray techniques, we were now able to elucidate the first solid-state structure of a Li/F alkyl carbenoid, pentafluoroethyllithium (LiC2F5), finally yielding a prototype for investigating structurereactivity relationships for this class of molecules. The compound forms a diethyl ether-solvated dimer bridged by a rare C-F-Li link. Complementary NMR spectroscopy studies in solution show dynamic processes and indicate rapid exchange of starting material and product. Theoretical investigations help to understand the formation of the observed unusual structural motif.
Erscheinungsjahr
Zeitschriftentitel
Angewandte Chemie International Edition
Band
53
Zeitschriftennummer
43
Seite
11640-11644
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Waerder B, Steinhauer S, Neumann B, et al. Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium. Angewandte Chemie International Edition. 2014;53(43):11640-11644.
Waerder, B., Steinhauer, S., Neumann, B., Stammler, H. - G., Mix, A., Vishnevskiy, Y., Hoge, B., et al. (2014). Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium. Angewandte Chemie International Edition, 53(43), 11640-11644. doi:10.1002/anie.201406564
Waerder, B., Steinhauer, S., Neumann, B., Stammler, H. - G., Mix, A., Vishnevskiy, Y., Hoge, B., and Mitzel, N. W. (2014). Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium. Angewandte Chemie International Edition 53, 11640-11644.
Waerder, B., et al., 2014. Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium. Angewandte Chemie International Edition, 53(43), p 11640-11644.
B. Waerder, et al., “Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium”, Angewandte Chemie International Edition, vol. 53, 2014, pp. 11640-11644.
Waerder, B., Steinhauer, S., Neumann, B., Stammler, H.-G., Mix, A., Vishnevskiy, Y., Hoge, B., Mitzel, N.W.: Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium. Angewandte Chemie International Edition. 53, 11640-11644 (2014).
Waerder, Benedikt, Steinhauer, Simon, Neumann, Beate, Stammler, Hans-Georg, Mix, Andreas, Vishnevskiy, Yury, Hoge, Berthold, and Mitzel, Norbert W. “Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium”. Angewandte Chemie International Edition 53.43 (2014): 11640-11644.

16 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

On Pentakis(pentafluoroethyl)stannate, [Sn(C2 F5 )5 ]- , and the Gas-Free Generation of Pentafluoroethyllithium, LiC2 F5.
Wiesemann M, Klösener J, Neumann B, Stammler HG, Hoge B., Chemistry 24(8), 2018
PMID: 29068093
Tris(pentafluoroethyl)stannane: Tin Hydride Chemistry with an Electron-Deficient Stannane.
Wiesemann M, Niemann M, Klösener J, Neumann B, Stammler HG, Hoge B., Chemistry 24(11), 2018
PMID: 29211312
Synthesis and Reactivity of Donor-Stabilized Bis(pentafluoroethyl)stannylene [Sn(C2 F5 )2 (D)n ] (D=THF, DMAP, PMe3 , [Sn(C2 F5 )3 ]- ).
Klösener J, Wiesemann M, Niemann M, Neumann B, Stammler HG, Hoge B., Chemistry 24(17), 2018
PMID: 29315901
Pentafluoroethyl Bismuth Compounds.
Solyntjes S, Bader J, Neumann B, Stammler HG, Ignat'ev N, Hoge B., Chemistry 23(7), 2017
PMID: 27862439
Taming Metal/Fluorine Carbenoids.
Molitor S, Feichtner KS, Gessner VH., Chemistry 23(11), 2017
PMID: 27906492
Gold(I) Fluorohalides: Theory and Experiment.
Baya M, Pérez-Bitrián A, Martínez-Salvador S, Casas JM, Menjón B, Orduna J., Chemistry 23(7), 2017
PMID: 27933670
The Tris(pentafluoroethyl)stannate(II) Anion, [Sn(C2 F5 )3 ]- -Synthesis and Reactivity.
Wiesemann M, Klösener J, Niemann M, Neumann B, Stammler HG, Hoge B., Chemistry 23(58), 2017
PMID: 28671288
Alkali Metal Carbenoids: A Case of Higher Stability of the Heavier Congeners.
Molitor S, Gessner VH., Angew Chem Int Ed Engl 55(27), 2016
PMID: 27100278
Synthesis of Functional Bis(pentafluoroethyl)silanes (C2 F5 )2 SiX2 , with X=H, F, Cl, Br, OPh, and O2 CCF3.
Schwarze N, Kurscheid B, Steinhauer S, Neumann B, Stammler HG, Ignat'ev N, Hoge B., Chemistry 22(48), 2016
PMID: 27778393
Nucleophilic Transfer Reactions of the [Si(C2 F5 )3 ]- Moiety.
Schwarze N, Steinhauer S, Neumann B, Stammler HG, Hoge B., Angew Chem Int Ed Engl 55(52), 2016
PMID: 27902862
The Tris(pentafluoroethyl)silanide Anion.
Schwarze N, Steinhauer S, Neumann B, Stammler HG, Hoge B., Angew Chem Int Ed Engl 55(52), 2016
PMID: 27902868
A Neutral Silicon/Phosphorus Frustrated Lewis Pair.
Waerder B, Pieper M, Körte LA, Kinder TA, Mix A, Neumann B, Stammler HG, Mitzel NW., Angew Chem Int Ed Engl 54(45), 2015
PMID: 26423202

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