Reactions of an isolable dialkylsilylene with dichloromethane and (chloromethyl)cyclopropane occur in solution to afford the double silylene insertion product and an unusual 5-silaspiro[4.4]nonane derivative, respectively. The activation of the carbon-chlorine bonds due to the complexation of haloalkanes with the silylene may facilitate the nucleophilic attack of another silylene under the present reaction conditions.