Reactions of stable silylenes 1 and 2 with a variety of halogenated organic compounds have been studied. Depending on the nature of the halocarbon, the products can be disilanes, LSiX-LSiR, or monosilanes, LSiXR, or a mixture of both types of products. Hexachloroethane reacts with the silylenes to give mainly the clichlorodisilane, LSiX-LSiX. The experimental results are rationalized in terms of several related free-radical chain mechanisms.