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Stannole is an organotin compound with the chemical formula (carbonhydrogen)4tin2. It is classified as a metallole, i.e. an unsaturated five-membered ring containing a heteroatom. It is a structural analog of cyclopentadiene, with tin replacing the saturated carbon atom. Substituted derivatives, which have been synthesized, are also called stannoles.
1,1-Dimethyl-2,3,4,5-tetraphenyl-1 H-stannole, for example, can be formed by the displacement reaction of 1,4-dilithio-1,2,3,4-tetraphenyl-1,3-butadiene and .
Palladium and cobalt catalyze a 2+2+1 cycloaddition between two acetylene molecules and a stannylene SnR2 to give the corresponding stannole.
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