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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Abstract
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.
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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.
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16 Citations in Europe PMC

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Pentafluoroethyl Bismuth Compounds.
Solyntjes S, Bader J, Neumann B, Stammler HG, Ignat'ev N, Hoge B., Chemistry 23(7), 2017
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Taming Metal/Fluorine Carbenoids.
Molitor S, Feichtner KS, Gessner VH., Chemistry 23(11), 2017
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Gold(I) Fluorohalides: Theory and Experiment.
Baya M, Pérez-Bitrián A, Martínez-Salvador S, Casas JM, Menjón B, Orduna J., Chemistry 23(7), 2017
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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
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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
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Nucleophilic Transfer Reactions of the [Si(C2 F5 )3 ]- Moiety.
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The Tris(pentafluoroethyl)silanide Anion.
Schwarze N, Steinhauer S, Neumann B, Stammler HG, Hoge B., Angew Chem Int Ed Engl 55(52), 2016
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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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