V. Jouikov, G. Salaheev
1996
Citations
0
Influential Citations
14
Citations
Journal
Electrochimica Acta
Abstract
Abstract Electrochemical reduction of chlorotrimethylsilane and dichlorodimethylsilane in the presence of phenylacetylene results in silylated ethynyl and ethenyl derivatives—phenyl(trimethylsilyl)acetylene and trimethylsilylstyrene. Under similar conditions, phenyl(trimethylsilyl)acetylene gives a product which corresponds to the addition of Me 3 Si − anion to the triple bond. By varying the conditions of the electrolysis (the ratio of the reagents, quantity of electricity passed and on carrying out the electrolysis in ECE-mode), either mono- (up to 82% yield) or disilylated (up to 61% yield) products were obtained. The use of the bifunctional chlorosilane as a silylating reagent results in dimethyl bis(phenylethynyl) silane (20% yield). The active silylating species of the process was shown to be the Me 3 Si − -anions, though some assistance from secondary silyl-radicals cannot be ignored. A mechanism of silylation is discussed.