Abstract Treating dichlorocarbene with 1-silacyclopent-2 (or-3)-ene leads to the corresponding bridged dichloro compounds. Thermal stability of these derivatives depends on the nature of the ring substituants and on the position of the bridge with respect to the heteroatom. In order to explain the structure of cyclic and linear products formed in thermolysis reaction, we propose two competitive mechanisms; one concerted, involving ...