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Trifluoromethylated Compounds with SiNN and SiON Backbone, and the Crystal Structures of Trimethyl- and Trichloro(trifluoromethyl)silane

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Trifluoromethylated Compounds with SiNN and SiON Backbone, and the Crystal Structures of Trimethyl- and Trichloro(trifluoromethyl)silane

Markus Woski and Norbert W. Mitzel

Lehrstuhl f¨ur Anorganische Chemie und Strukturchemie, Universit¨at Bielefeld, Universit¨atsstraße 25, 33615 Bielefeld, Germany

Reprint requests to Prof. Dr. N. W. Mitzel. Fax: (+49)521 106 6026. E-mail: mitzel@uni-bielefeld.de Z. Naturforsch.2009,64b,83 – 92; received October 2, 2008

Dedicated to Professor Otto J. Scherer on the occasion of his 75thbirthday

The reaction of (F3C)Cl2SiCl3 with the lithiated hydrazine LiN(Me)NMe2 gives the com- pound (F3C)Cl2SiN(Me)NMe2 (1) and in traces Cl3SiN(Me)NMe2 (2). The reactions with LiN(SiMe3)NMe2and LiONMe2 give (F3C)Cl2SiN(SiMe3)NMe2 (4) and (F3C)Cl2SiONMe2(5), respectively. The compounds were characterised by multinuclear solution NMR, gas-phase IR spec- troscopy and mass spectrometry. Information about conformational preferences of1and4can be extracted by comparing experimental IR spectra with those calculated by quantum chemical methods (B3LYP/6-311G**). The former show the gas phase of theβ-donor-acceptor silanes1and4to be dominated by theanticonformations, while the calculations show a preference for thegauchecon- formers. The crystal structure of Cl3SiN(Me)NMe2 (2) has been determined. The solid-state struc- tures of the Ruppert reagent F3C–SiMe3(1) and its chlorine analogue F3C–SiCl3(2) have also been determined by X-ray diffraction of single crystals grown byin situtechniques.

Key words:Silicon, Trifluoromethylsilanes, Hydroxylamine, Hydrazine, Crystal Structure, Quantum Chemical Calculations

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