Stannole
Organotin compound
From Wikipedia, the free encyclopedia
Stannole is an organotin compound with the formula (CH)4SnH2. 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]
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| Names | |||
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| Preferred IUPAC name
1H-Stannole | |||
| Identifiers | |||
3D model (JSmol) |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |||
| C4H6Sn | |||
| Molar mass | 172.802 g·mol−1 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Examples
1,1-Dibutylstannole is a pale yellow oil prepared from 1,4-dilithio-1,3-butadiene and dibutyltin dichloride.[2]
1,1-Dimethyl-2,3,4,5-tetraphenyl-1H-stannole, for example, can be formed by the displacement reaction of 1,4-dilithio-1,2,3,4-tetraphenyl-1,3-butadiene and dimethyltin dichloride.[3]
Palladium and cobalt catalyze a [2+2+1] cycloaddition between two acetylene molecules and a stannylene SnR2 to give the corresponding stannole.[4]
Related compounds
1λ2-Stannole has formula C4H4Sn, with no hydrogen on the tin atom, which is in the +2 oxidation state.[5]