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

Various nucleophiles were reacted with the substrate di-n-hexyldichlorosila ne as model reactions for the substitution of two geminal Si-CI bonds on po lymer backbone repeat units. The reactants examined were chosen on the basi s of steric bulk, electronic factors, and resulting stability of the produc t. Linear and branched alcohol nucleophiles used in conjunction with an ami ne proton acceptor produced disubstituted products in moderate yields, wher eas bulkier reagents substituted only one silicon-chlorine bond. Due to the ir vastly increased nucleophilicity, alkyllithium reagents were found to ha ve increased activity and were found to produce very high yields. (C) 2001 Elsevier Science B.V. All rights reserved.