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The syntheses of tetra(dichlorocyclopropane)silane <b>2</b> and tetra(cyclo- propane)silane <b>3</b> have been accomplished using dichlorocarbene (:CCl2) and carbenoid addition, respectively. Various phase transfer catalysts (PTC) have been tested for :CCl2 addition to tetraallylsilane <b>1</b>. 2-Benzilidine-N,N,N,N',N',N',-hexaethyl propane-1,3-diammonium dibromide (Dq-Br) was found to be effective in giving <b>2</b> in a yield above 80%. A modified synthetic route to <b>3</b> by the reaction of <b>1</b> with Zn-Ag couple and methylene iodide is also described. The success of the reaction has been attributed to an alternative work-up procedure.