Two novel carbene-stabilized silacyclopentadienylidenes have been obtained via dehydrohalogenation of the corresponding hydrochlorosilole with N-heterocyclic carbenes in THF at low temperature. The base-stabilized cyclic carbon substituted silylenes are highly nucleophilic, as exemplified by the nucleophilic attack on phenylacetylene to give a luminescent 1-alkenyl-1-alkynylsilole with the liberation of the coordinated carbene.