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