Stibole
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| Names | |||
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| Preferred IUPAC name
1H-Stibole | |||
| Identifiers | |||
3D model (JSmol) |
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| ChemSpider | |||
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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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.
Preparation
[edit source]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
[edit source]Stibolides (C4R4Sb−) form half-sandwich compounds.[4]
See also
[edit source]References
[edit source]- ↑ Leavitt, F. C.; Manuel, T. A.; Johnson, F.; Matternas, L. U.; Lehman, D. S. (1960). "Novel Heterocyclopentadienes. II". Journal of the American Chemical Society. 82 (19): 5099–5102. Bibcode:1960JAChS..82.5099L. doi:10.1021/ja01504a021.
- ↑ Ashe, Arthur J.; Drone, Frederick J. (1985). "Synthesis of 1-phenylarsole and 1-phenylstibole". Organometallics. 4 (8): 1478–1480. doi:10.1021/om00127a038.
- ↑ J.I.G. Cadogan; S.V. Ley; G. Pattenden; R.A. Raphael; C.W. Rees, eds. (1996), Dictionary of Organic Compounds, vol. 3 (6 ed.), Chapman & Hall, p. 2710, ISBN 978-0-412-54090-5, retrieved 2010-03-04
- ↑ A.R. Katritzky; Otto Meth-Cohn; C.W. Rees, eds. (1995), Comprehensive Organic Functional Group Transformations, vol. 4, Elsevier, pp. 1038–1040, ISBN 978-0-08-042325-8, retrieved 2010-03-04
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