The reactions of bridged tris(trimethylsilyl)silyl fragments with 2 molar equiv of potassium tert-butoxide allow the generation of α,ω-oligosilyl dianions (1a, 2a, 3a, 4a). Depending on the nature of the spacer between the oligosilyl units, these compounds can be used to generate either linear or cyclic derivatives. They are especially attractive for the formation of homo- and heterocyclosilanes, as