Syntheses and Molecular Structures of Hexasilylbenzenes and Disilylacetylenes

Christoph Rudinger, Peter Blssinger, Holger Beruda, Hubert Schmidbaur

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Abstract

For the preparation of bis(phenylsilyl)acetylene (2), Li2C2 has been obtained from Br2CHCHBr2 (or ClCHCHCl) and alkyllithium reagents and reacted with ClSiH2Ph. HC2Na and BrSiH2Ph afford the primary product HC2SiH2Ph (4), from which, via metalation and treatment with H3SiBr, H3SiC2SiH2Ph (5) can be generated. 2 could not be trimerized when treated with various transition metal catalysts. Hexakis- (phenylsilyl)benzene (1) is available from the reaction of PhSiH2Cl and C6Br6 with Mg in tetrahydrofuran, and the p-tolyl analogue 3 has been prepared similarly using p-TolSiH2Cl. The crystal and molecular structures of 1-3 have been determined by single-crystal X-ray diffraction. 2 has standard disilylalkyne dimensions. In contrast to the hexakis(trimethylsilyl) analogue, 1 and 3 feature planar central benzene rings with the arylsilyl groups at opposite corners above and below the plane. 1 crystallizes from CCl4 with two independent molecules and three solvent molecules of CCl4 in the asymmetric unit (rhombohedral, space group R3). Both I and 3 crystallize from ethyl acetate without solvent, but only the structure of 3 has been determined (rhombohedral, space group R3). 2 crystallizes from the melt (monoclinic, space group P21/a).

Original languageEnglish
Pages (from-to)2867-2873
Number of pages7
JournalOrganometallics
Volume11
Issue number8
DOIs
StatePublished - 1 Aug 1992
Externally publishedYes

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