Stibole
Chemical compound
From Wikipedia, the free encyclopedia
Stibole is a heterocyclic organic compound, a five-membered ring with the formula C4H4SbH. It is classified as a metallole. It can be viewed as a structural analog of pyrrole, with antimony replacing the nitrogen atom of pyrrole. Stibole itself has not been isolated, but many substituted derivatives have been synthesized. They are called stiboles.
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| Names | |||
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| Preferred IUPAC name
1H-Stibole | |||
| Identifiers | |||
3D model (JSmol) |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |||
| C4H5Sb | |||
| Molar mass | 174.844 g·mol−1 | ||
| Related compounds | |||
Related compounds |
Pyrrole, phosphole, arsole, bismole | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
Pentaphenylstibile is prepared from 1,4-dilithio-1,2,3,4-tetraphenylbutadiene and phenylantimony dichloride by a salt metathesis reaction:[1]
- LiCPh=CPh−CPh=CPhLi + PhSbCl2 → Ph4C4SbPh + 2 LiCl (Ph = C6H5)
Even simpler than the above, 1-phenylstibole can be prepared analgously from 1,4-dilithiobutadiene. It is yellow oil that resinifies at room temperature.[2]
2,5-Dimethyl-1-phenyl-1H-stibole, for example, can be formed by the reaction of 1,1-dibutyl-2,5-dimethylstannole and dichlorophenylstibine.[3]
Derivatives
Stibolides (C4R4Sb−) form half-sandwich compounds.[4]
