Carboranyl-containing disiloxane, cyclic-siloxane and cage-like silsesquioxane have been prepared in high yields. Two routes are compared for their preparation, a classical hydrolytic process based on hydrolysis and condensation of the freshly prepared carboranylalkylchlorosilane and ethoxysilane precursors and a nonhydrolytic route based on the specific reactivity of chorosilane toward DMSO. Based on the typical reactivity of the carboranyl group toward nucleophiles, dianionic disiloxanes and octaanionic silsesquioxanes were obtained without modification of the siloxane bond. Products are fully characterized by FTIR, NMR and MALDI-TOF methods.