A Wurtz-type reductive coupling reaction of dichlorophenyl-alpha-naphthylsilane was carried out in a mixture of toluene and o-xylene in the presence of sodium and a catalytic amount of mercury; alpha,omega-dichlorophenyl-alpha-naphthylsilylenes of various degrees of polymerization were obtained. Through the hydrolysis of alpha,omega-dichlorophenyl-alpha-naphthylsilylenes, corresponding dihydroxy compounds were obtained. The heterofunctional polycondensation of alpha,omega-dihydroxyphenyl-alpha-naphthylsilylenes with alpha,omega-dichlorodimethylsilylenes was performed both without amines and in the presence of amines. Heterofunctional polycondensation without amines did not proceed with the formation of high molecular weight compounds because the cleavage of both equivalent toSi-Siequivalent to and equivalent toSi-O-Siequivalent to bonds took place during condensation. In the presence of amines, polysilylene-silylene copolymers were obtained. The synthesized copolymers were investigated with gel permeation chromatography, differential scanning calorimetry, roentgenography, and thermogravimetry.