Untersuchungen zur Einführung der polyfluorierten Gruppen CF3(CF2)5-C2H4 und C6F5 in Alkyl- und Arylchlorsilane

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This thesis describes the syntheses of the silanes, Bis(1H,1H,2H,2H-tridecafluorooctyl)dichlorosilane, Tris(1H,1H,2H,2H-tridecafluorooctyl)chlorosilane and Tetrakis(1H,1H,2H,2H-tridecafluorooctyl)silane. The Polyfluorooctylchlorosilanes were obtained by the reaction of Phenylchlorosilanes with stoichiometric amounts of Tridecafluorooctyllithium in Ether at -40 °C to give the Phenyl(tridecafluorooctyl)silanes, which were further reacted with Aluminiumtrichloride in Dichloromethane. Tetrakis(1H,1H,2H,2H-tridecafluorooctyl)silane has been synthesized by reaction of Tridecafluorooctyllithium with Tetrachlorosilane in Ether at -40 °C. Systematic investigations on the reactivity of Alkyl- and Arylchlorosilanes towards nucleophilic reactants, such as C6F13C2H4MgBr, C6F13C2H4MgI, C6F5MgBr and C6F5MgI were undertaken. Within these investigations we have shown that Tridecafluorooctylmagnesium bromide is suitable to introduce a long-chain fluoroorganyl group into Bis(pentafluorphenyl)dichlorosilane forming the tetravalent Bis(pentafluorophenyl)bis(tridecafluorooctyl)silane. No reaction occurred when changing the strongly electron withdrawing pentafluorophenyl group with its proton analoque, which likely arises from electronic but not from steric aspects. The complete assignments of the 19F- and 13C-NMR spectra of Tridecafluorooctyliodide as well as of several Tridecafluorooctylsilanes were solved using combinations of 1D and 2D NMR experiments.
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Dokumententyp:
Wissenschaftliche Abschlussarbeiten » Dissertation
Fakultät / Institut:
Fakultät für Chemie
Dewey Dezimal-Klassifikation:
500 Naturwissenschaften und Mathematik » 540 Chemie
Stichwörter:
Bis(tridecafluorooctyl)dichlorosilane, Phenyl(tridecafluorooctyl)silane, C6F13C2H4, Tris(tridecafluorooctyl)chlorosilane, Ponytail, NMR spectroscopy, Pentafluorophenyl(tridecafluorooctyl)silane, Organosilanes
Beitragende:
Prof. Dr. rer. nat. Frohn, Hermann-Josef [Betreuer(in), Doktorvater]
Priv.-Doz. Dr. Köckerling, Martin [Gutachter(in), Rezensent(in)]
Sprache:
Deutsch
Kollektion / Status:
Dissertationen / Dokument veröffentlicht
Datum der Promotion:
04.02.2004
Dokument erstellt am:
04.02.2004
Dateien geändert am:
18.10.2006
Medientyp:
Text