The synthesis of perfluorinated compounds by direct fluorination: organometallic compounds and carboranes
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The use and modification of the Exfluor-Lagow direct fluorination technique has been used to perfluorinate tetraalkylgemanes, tetraethylsilane, and methylated carborane compounds. Perfluorianted tetraalkylgermanes and tetraalkylsilanes synthesized by direct fluorination from the corresponding hydrocarbon germanes and silanes are: Perfluorotetraethylgerman, Perfluorotetra-n-propylgermane, Perfluorotetra-nbutylgerman and Perfluorotetraethylsilane. All perfluorinated germanes and silanes vi were characterized by 19F NMR spectroscopy as well as low and high resolution mass spectroscopy. Dodecamethyl-1,12-dicarba-closo-dodecarborane (1,12-(CH3)2-1,12- C2B10(CH3)10), was perfluorinated using an elevated temperature fluorination apparatus, and characterized by both 19F, and 11B NMR. Decamethyl-1,12-dicarbacloso-dodecacarborane (1,12-(H)2-1,12-C2B10(CH3)10) was fluorinated with retention of the C-H verticies at the 1,12 position, and it was structurally was determined by Xray crystallography, 19F and 11B NMR spectroscopy, as well as low and high resolution mass spectroscopy. Decamethyl-1,12-dicarba-closo-dodecacarborane (1,12-(H)2-1,12-C2B10(CH3)10) was also perfluorinated (conversion of the C-H verticies to C-F, at the 1,12 position), and its structure was determined by X-ray crystallography, 19F and 11B NMR spectroscopy, as well as low and high resolution mass spectroscopy. Perfluorodecamethyl-1,12-dicarba-closo-dodecacarborane represents the first structurally characterized perfluorinated icosahedral borane derivative. The fluorination of dodecamethyl-closo-dodecaborane B12(CH3)12 2- was investigated.