SYNTHESIS, PROPERTIES AND REACTIONS OF SILA-FUNCTIONAL ALPHA-HETEROATOM-SUBSTITUTED ORGANOSILICON COMPOUNDS

Several types of sila-functional alpha-heteroatom-substituted organosi licon compounds were synthesized. Alpha-Heteroatom-substituted hydrosi lanes were prepared by the reaction of the corresponding alpha-heteroa tom-substituted carbanions with chlorodiorganosilanes. Alpha-Heteroato m-substituted alkoxysilanes were synthesized by chlorination of alpha- heteroatom-substituted hydrosilanes with PdCl2/CCl4 followed by reacti on with alcohols in the presence of triethylamine. Alpha-Heteroatom-su bstituted fluorosilanes were obtained by direct CuF2.2H2O/CCl4 promote d fluorination of the corresponding hydrosilanes. Electrochemical oxid ation potentials of sila-functional alpha-heteroatom-substituted organ osilicon compounds were determined. The introduction of a hydrogen or a fluorine substituent on the silicon caused a small increase in the o xidation potentials, which is consistent with the results of molecular orbital calculations. Preparative anodic oxidation of alpha-heteroato m-substituted hydro- and fluorosilanes in methanol resulted in the cle avage of the carbon-silicon bond and introduction of the methoxyl grou p onto the carbon. Hydrosilylation of olefins with alpha-heteroatom-su bstituted hydrosilanes proceeded smoothly providing a useful method fo r the preparation of alpha-heteroatom-substituted organosilicon compou nds.