An examination of the substitution chemistry of di-n-hexyldichlorosilane

Various nucleophiles were reacted with the substrate di-n-hexyldichlorosilane as model reactions for the substitution of two geminal SiCl bonds on polymer backbone repeat units. The reactants examined were chosen on the basis of steric bulk, electronic factors, and resulting stability of the product. Linear and branched alcohol nucleophiles used in conjunction with an amine proton acceptor produced disubstituted products in moderate yields, whereas bulkier reagents substituted only one siliconchlorine bond. Due to their vastly increased nucleophilicity, alkyllithium reagents were found to have increased activity and were found to produce very high yields.