Synthesis of Mono‐, Bis‐ and Tris(pentafluoroethyl)tin Derivatives, (C2F5)4−nSnXn (X=Ph, Me, Cl, Br, Cp; n=1–3)
For (pentafluoroethyl)phenylstannanes, (C 2 F 5 ) 4− n SnPh n ( n =1–3), and dimethylbis(pentafluoroethyl)stannane, (C 2 F 5 ) 2 SnMe 2 , a high yield synthesis was developed by the use of LiC 2 F 5 as a C 2 F 5 transfer reagent. The treatment of these products with gaseous hydrogen chloride or hydrogen bromide afforded (C 2 F 5 ) 4− n SnX n (X=Cl, Br; n =1–3) in good yields. The (pentafluoroethyl)stannanes were fully characterized by 1 H, 13 C, 19 F and 119 Sn NMR, IR spectroscopy and mass spectrometry. The treatment of the (pentafluoroethyl)tin halides (C 2 F 5 ) 4− n SnX n with 1,10‐phenanthroline (phen) led to the formation of the corresponding octahedrally coordinated complexes [(C 2 F 5 ) 4− n SnX n (phen)], the structures of which were elucidated by X‐ray diffraction analyses. The bromostannane (C 2 F 5 ) 3 SnBr reacted with sodium cyclopentadienide to give the ( η 1 ‐cyclopentadienyl)tris(pentafluoroethyl)stannane, (C 2 F 5 ) 3 SnCp, for which single‐crystal X‐ray diffraction analysis could be performed. The coupling constants 1 J ( 119 Sn, 13 C) and 2 J ( 119 Sn, 19 F) 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. Some‐tin special : We present a convenient protocol for the high yield synthesis of (pentafluoroethyl)stannanes ( n =1–3) by using LiC 2 F 5 . (Pentafluoroethyl)phenylstannanes are functionalized by gaseous hydrogen halides HX (X=Cl, Br) to give (pentafluoroethyl)tin halides. Their corresponding 1,10‐phenanthroline (phen) complexes were structurally characterized by X‐ray diffraction analysis..
| Medienart: |
Artikel |
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| Erscheinungsjahr: |
2017 |
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| Erschienen: |
2017 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:23 |
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| Enthalten in: |
Chemistry - a European journal - 23(2017), 34, Seite 8295-8303 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Klösener, Johannes [VerfasserIn] |
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| Links: |
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| RVK: |
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| doi: |
10.1002/chem.201701270 |
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| PPN (Katalog-ID): |
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| 245 | 1 | 0 | |a Synthesis of Mono‐, Bis‐ and Tris(pentafluoroethyl)tin Derivatives, (C2F5)4−nSnXn (X=Ph, Me, Cl, Br, Cp; n=1–3) |
| 264 | 1 | |c 2017 | |
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| 520 | |a For (pentafluoroethyl)phenylstannanes, (C 2 F 5 ) 4− n SnPh n ( n =1–3), and dimethylbis(pentafluoroethyl)stannane, (C 2 F 5 ) 2 SnMe 2 , a high yield synthesis was developed by the use of LiC 2 F 5 as a C 2 F 5 transfer reagent. The treatment of these products with gaseous hydrogen chloride or hydrogen bromide afforded (C 2 F 5 ) 4− n SnX n (X=Cl, Br; n =1–3) in good yields. The (pentafluoroethyl)stannanes were fully characterized by 1 H, 13 C, 19 F and 119 Sn NMR, IR spectroscopy and mass spectrometry. The treatment of the (pentafluoroethyl)tin halides (C 2 F 5 ) 4− n SnX n with 1,10‐phenanthroline (phen) led to the formation of the corresponding octahedrally coordinated complexes [(C 2 F 5 ) 4− n SnX n (phen)], the structures of which were elucidated by X‐ray diffraction analyses. The bromostannane (C 2 F 5 ) 3 SnBr reacted with sodium cyclopentadienide to give the ( η 1 ‐cyclopentadienyl)tris(pentafluoroethyl)stannane, (C 2 F 5 ) 3 SnCp, for which single‐crystal X‐ray diffraction analysis could be performed. The coupling constants 1 J ( 119 Sn, 13 C) and 2 J ( 119 Sn, 19 F) 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. Some‐tin special : We present a convenient protocol for the high yield synthesis of (pentafluoroethyl)stannanes ( n =1–3) by using LiC 2 F 5 . (Pentafluoroethyl)phenylstannanes are functionalized by gaseous hydrogen halides HX (X=Cl, Br) to give (pentafluoroethyl)tin halides. Their corresponding 1,10‐phenanthroline (phen) complexes were structurally characterized by X‐ray diffraction analysis. | ||
| 540 | |a Nutzungsrecht: © 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim | ||
| 650 | 4 | |a halogens | |
| 650 | 4 | |a stannanes | |
| 650 | 4 | |a perfluoroalkyl | |
| 650 | 4 | |a fluorine | |
| 650 | 4 | |a pentafluoroethyl | |
| 650 | 4 | |a Infrared spectroscopy | |
| 650 | 4 | |a X ray diffraction | |
| 650 | 4 | |a Hydrogen bromide | |
| 650 | 4 | |a Single crystals | |
| 650 | 4 | |a Chlorides | |
| 650 | 4 | |a Mass spectrometry | |
| 650 | 4 | |a Chloride | |
| 650 | 4 | |a Hydrogen | |
| 650 | 4 | |a Correlation | |
| 650 | 4 | |a Spectroscopy | |
| 650 | 4 | |a X-ray diffraction | |
| 650 | 4 | |a Halides | |
| 650 | 4 | |a Mass spectroscopy | |
| 650 | 4 | |a Spectrometry | |
| 650 | 4 | |a Sodium | |
| 650 | 4 | |a Coupling | |
| 650 | 4 | |a Derivatives | |
| 650 | 4 | |a I.R. spectroscopy | |
| 650 | 4 | |a Diffraction | |
| 650 | 4 | |a Tin | |
| 650 | 4 | |a Synthesis | |
| 700 | 1 | |a Wiesemann, Markus |4 oth | |
| 700 | 1 | |a Niemann, Mark |4 oth | |
| 700 | 1 | |a Neumann, Beate |4 oth | |
| 700 | 1 | |a Stammler, Hans‐Georg |4 oth | |
| 700 | 1 | |a Hoge, Berthold |4 oth | |
| 773 | 0 | 8 | |i Enthalten in |t Chemistry - a European journal |d Weinheim : Wiley-VCH, 1995 |g 23(2017), 34, Seite 8295-8303 |w (DE-627)185258727 |w (DE-600)1231884-X |w (DE-576)046705821 |x 0947-6539 |7 nnns |
| 773 | 1 | 8 | |g volume:23 |g year:2017 |g number:34 |g pages:8295-8303 |
| 856 | 4 | 1 | |u http://dx.doi.org/10.1002/chem.201701270 |3 Volltext |
| 856 | 4 | 2 | |u http://onlinelibrary.wiley.com/doi/10.1002/chem.201701270/abstract |
| 856 | 4 | 2 | |u https://search.proquest.com/docview/1910743763 |
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