Synthesis, Structure, and Reactivity of a 1-Stannavinylidene-NHC Complex: A Heavier Group-14 Analogue of Vinylidene.

The first stable 1-stannavinylidene-NHC complex with bulky silyl substituents has been obtained from the retro-dimerization of cyclic 1,3-bis(stannylene) with an N-heterocyclic carbene (NHC). To accomplish the retro-dimerization of cyclic 1,3-bis(stannylene), a suitably sized NHC is required. Both in the solid state and in solution, 1-stannavinylidene-NHC complex is characterized by the presence of a C = Sn π bond. When treated with SnCl, 1-stannavinylidene-NHC complex undergoes an addition reaction to afford the corresponding stable gem-bis(chlorostannylene).