Reaction of carboxylic acids with tetrachlorosilane |
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Authors: | M G Voronkov A V Vlasov L I Belousova O Yu Grigor’eva N N Vlasova |
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Institution: | (1) Department of Chemistry, Yeungnam University, Gyongsan, 712-749, Korea |
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Abstract: | Tetrachlorosilane reacted with carboxylic acids RCOOH (R = Me, Bu, t-Bu) to give the corresponding acid chlorides RCOCl in 75–95% yield. The reactions of SiCl4 with trichloroacetic and 2-fluorobenzoic acids (R = Cl3C, 2-FC6H4) occurred more difficultly, presumably for steric reasons, and the yields of the corresponding acid chlorides were 11 and
22%, respectively. Tetrachlorosilane failed to react with stearic acid under analogous conditions. Products of the reactions
of SiCl4 with chloroacetic and benzoic acids RCOOH (R = ClCH2, Ph) were tetraacyloxysilanes Si(OCOR)4, and tetrakis(chloroacetoxy)silane was formed in almost quantitative yield. The reaction of SiCl4 with glutaric acid led to the formation of a rubber-like polymeric material with the composition C5H6Cl2O4Si. The effect of pKa values of carboxylic acids on the direction and mechanism of the examined reaction is discussed. |
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