The reactivity of a bulky, diaryl-substituted disilyne, Ar-Si Si-Ar, was examined for the first time. Reaction of the disilyne with ethylene yielded an ethylene-bridged bis(silacyclopropane), which is interpreted as a Further reaction product of the initially formed 1,2-disilacyclobutene species with ethylene. A cyclohexane fused with a 1,2-disilacyclobutene was obtained in the reaction with cyclohexene. In the reaction with 2,3-dimethyl-1,3-butadiene, a tricyclo derivative was isolated from the complex product mixture.