Stannyloligosilanes 1 and 2 with terminal organotin groups are available by reacting alkali metal tri- or diorganostannides with α,ω-dichloro- or difluorosilanes, or by treatment of organochlorostannanes with α,ω-difluorosilanes in the presence of magnesium . Attempts to functionalize the triorganotin derivatives 2 by halogenation reagents did not result in the halogen compounds 5; instead cleavage of silicon-tin bonds is observed. In contrast, reactions of the hydridotin derivatives 1 with CHX3 (X = Cl, Br) lead to the quantitative formation of the bis(chloro- or bromostannyl)oligosilanes 5. A ll compounds were characterized by NMR, IR, MS and elemental analysis. In addition, the triorganotin compound 2i and the hydridotin species 1b have been characterized by X-ray crystallography.