Journal article
Reduction of Terphenyltrifluorosilanes: C-C Insertion Products and Possible Formation of a Disilyne.



Publication Details
Authors:
Pietschnig, R.; West, R.; Powell, D.
Publisher:
American Chemical SocietyDO - 10.1021/om990924z
Publication year:
2000
Journal:
Organometallics
Pages range:
2724-2729
Volume number:
19
Start page:
2724
End page:
2729
ISSN:
0276-7333

Abstract
Terphenyl trifluorosilanes, 2,6-Mes2C6H3SiF3 (1) and 2,6-Tip2C6H3SiF3 (2), were synthesized, and their redn. behavior was studied. Redn. with Na in both cases results in insertion of the Si center into C-C bonds of the substituent. The reactive intermediates giving rise to the C-C insertion most likely involve fluorosilylene or disilyne species. The final product is a bis-silafluorenyl (3) in the case of 1 and a silafluorenyl anion in the case of 2. The anion can be protonated to give a stable silafluorene. The redn. of 1 and 2 with K gives a completely different result, and radical species are formed instead. The different reaction pathway is probably caused by the existence of a poorly sol. intermediate [2Mes2C6H3SiF3·3KF] (10) that lowers the concn. of the starting material and therefore influences the reaction kinetics. Crystal structures are presented for 1, 2, the insertion product 3, and the intermediate adduct 10. [on SciFinder(R)]


Keywords
crystal structure terphenyltrifluorosilane bissilafluorenyl hexacoordinate terphenylpentafluorosilicate intermediate, fluorosilicate terphenyl hexacoordinate pentacoordinate bridging potassium prepn crystal structure, mol structure terphenyltrifluorosilane bissilafluorenyl hexacoordinate terphenylpentafluorosilicate intermediate, silafluorenyl dimer prepn crystal structure, tetrafluorosilane lithiation condensation terphenyl halide


Authors/Editors

Last updated on 2019-25-07 at 16:00