Abstract
Treatment of 1,1,3,3-tetrakis(alkylthio)-2-silapropanes with t-BuLi in THF at -40 °C generated 1,1,3,3-tetrakis(alkylthio)-1,3-dilithio-2-silapropanes which reacted with various bifunctional chlorosilanes to give the corresponding 4- to 7-membered polysilacycloalkanes in moderate to good yields. Furthermore, double alkylation of the dilithiated silanes with bis(halomethyl)diorganosilanes or dihaloalkanes was found to proceed smoothly giving rise to 1,4-disilacyclohexanes or silacycloalkanes in good yields, respectively, in THF and an aprotic polar co-solvent such as hexamethylphosphoric triamide (HMPA) or 1,1,3,3-tetramethylurea (TMU). The sulfenyl groups in the cyclized products were smoothly removed by radical reduction with tributyltin hydride.
Highlights
Growing interest has been paid on polysilacycloalkanes, cycloalkanes containing one or more silicon atoms in the ring, as target molecules or precursors of polymers, ceramics, and functional materials as well as in the hypervalent silicon chemistry
We report here facile synthesis of polysilacycloalkanes via the reactions of 1 (Z1, Z2 = SR) with bis(chlorosilane)s or bis(alkyl halide)s
Using the solvent system consisting of THF and TMU, and bis(bromomethyl)silanes as an alkylating reagent, 1,4-disilacyclohexanes 8b-f having various substituents on silicon were prepared as colorless plates
Summary
Growing interest has been paid on polysilacycloalkanes, cycloalkanes containing one or more silicon atoms in the ring, as target molecules or precursors of polymers, ceramics, and functional materials as well as in the hypervalent silicon chemistry.
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