Synthesis of Mono-, Bis- and Tris(pentafluoroethyl)tin Derivatives, (C2F5)(4-n)SnXn (X = Ph, Me, Cl, Br, Cp; n=1-3)

Klösener J, Wiesemann M, Niemann M, Neumann B, Stammler H-G, Hoge B (2017)
CHEMISTRY-A EUROPEAN JOURNAL 23(34): 8295-8303.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
For (pentafluoroethyl) phenylstannanes, (C2F5)(4-n)SnPhn (n=1-3), and dimethylbis(pentafluoroethyl)stannane, (C2F5)(2)SnMe2, a high yield synthesis was developed by the use of LiC2F5 as a C2F5 transfer reagent. The treatment of these products with gaseous hydrogen chloride or hydrogen bromide afforded (C2F5)(4-n)SnXn (X=Cl, Br; n=1-3) in good yields. The (pentafluoroethyl) stannanes were fully characterized by H-1, C-13, F-19 and Sn-119 NMR, IR spectroscopy and mass spectrometry. The treatment of the (pentafluoroethyl)tin halides (C2F5)(4-n)SnXn with 1,10-phenanthroline (phen) led to the formation of the corresponding octahedrally coordinated complexes [(C2F5)(4-n)SnXn(phen)], the structures of which were elucidated by X-ray diffraction analyses. The bromostannane (C2F5)(3)SnBr reacted with sodium cyclopentadienide to give the (eta(1)-cyclopentadienyl) tris(pentafluoroethyl) stannane, (C2F5)(3)SnCp, for which single-crystal X-ray diffraction analysis could be performed. The coupling constants (1)J(Sn-119, C-13) and (2)J(Sn-119, F-19) of all new stannanes are strongly correlated and sensitive to the substitution pattern at the tin atom. For both coupling constants a negative sign could be assigned.
Stichworte
fluorine; halogens; pentafluoroethyl; perfluoroalkyl; stannanes
Erscheinungsjahr
2017
Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
23
Ausgabe
34
Seite(n)
8295-8303
ISSN
0947-6539
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/2912679

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Klösener J, Wiesemann M, Niemann M, Neumann B, Stammler H-G, Hoge B. Synthesis of Mono-, Bis- and Tris(pentafluoroethyl)tin Derivatives, (C2F5)(4-n)SnXn (X = Ph, Me, Cl, Br, Cp; n=1-3). CHEMISTRY-A EUROPEAN JOURNAL. 2017;23(34):8295-8303.
Klösener, J., Wiesemann, M., Niemann, M., Neumann, B., Stammler, H. - G., & Hoge, B. (2017). Synthesis of Mono-, Bis- and Tris(pentafluoroethyl)tin Derivatives, (C2F5)(4-n)SnXn (X = Ph, Me, Cl, Br, Cp; n=1-3). CHEMISTRY-A EUROPEAN JOURNAL, 23(34), 8295-8303. doi:10.1002/chem.201701270
Klösener, Johannes, Wiesemann, Markus, Niemann, Mark, Neumann, Beate, Stammler, Hans-Georg, and Hoge, Berthold. 2017. “Synthesis of Mono-, Bis- and Tris(pentafluoroethyl)tin Derivatives, (C2F5)(4-n)SnXn (X = Ph, Me, Cl, Br, Cp; n=1-3)”. CHEMISTRY-A EUROPEAN JOURNAL 23 (34): 8295-8303.
Klösener, J., Wiesemann, M., Niemann, M., Neumann, B., Stammler, H. - G., and Hoge, B. (2017). Synthesis of Mono-, Bis- and Tris(pentafluoroethyl)tin Derivatives, (C2F5)(4-n)SnXn (X = Ph, Me, Cl, Br, Cp; n=1-3). CHEMISTRY-A EUROPEAN JOURNAL 23, 8295-8303.
Klösener, J., et al., 2017. Synthesis of Mono-, Bis- and Tris(pentafluoroethyl)tin Derivatives, (C2F5)(4-n)SnXn (X = Ph, Me, Cl, Br, Cp; n=1-3). CHEMISTRY-A EUROPEAN JOURNAL, 23(34), p 8295-8303.
J. Klösener, et al., “Synthesis of Mono-, Bis- and Tris(pentafluoroethyl)tin Derivatives, (C2F5)(4-n)SnXn (X = Ph, Me, Cl, Br, Cp; n=1-3)”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 23, 2017, pp. 8295-8303.
Klösener, J., Wiesemann, M., Niemann, M., Neumann, B., Stammler, H.-G., Hoge, B.: Synthesis of Mono-, Bis- and Tris(pentafluoroethyl)tin Derivatives, (C2F5)(4-n)SnXn (X = Ph, Me, Cl, Br, Cp; n=1-3). CHEMISTRY-A EUROPEAN JOURNAL. 23, 8295-8303 (2017).
Klösener, Johannes, Wiesemann, Markus, Niemann, Mark, Neumann, Beate, Stammler, Hans-Georg, and Hoge, Berthold. “Synthesis of Mono-, Bis- and Tris(pentafluoroethyl)tin Derivatives, (C2F5)(4-n)SnXn (X = Ph, Me, Cl, Br, Cp; n=1-3)”. CHEMISTRY-A EUROPEAN JOURNAL 23.34 (2017): 8295-8303.

6 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
Pentafluoroethylated Compounds of Silicon, Germanium and Tin.
Wiesemann M, Hoge B., Chemistry 24(62), 2018
PMID: 29722451
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
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