Borole
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| Names | |||
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| IUPAC name
1H-Borole
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| Identifiers | |||
3D model (JSmol)
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| ChemSpider | |||
CompTox Dashboard (EPA)
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| Properties | |||
| C4H5B | |||
| Molar mass | 63.89 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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Borole is a theoretical heterocyclic organic compound, a five-membered ring with the formula C4H4BH. It is classified as a metallole. It can be viewed as an structural analog of pyrrole, with boron replacing the nitrogen atom of pyrrole. The unsubstituted compound has not been isolated. Substituted derivatives, which have been synthesized, are called boroles. Although the Hückel's rule cannot be strictly applied to borole, it is considered to be anti-aromatic.[1]
Reactions
The first borole to be isolated, pentaphenylborole, can be formed by the reaction of 1,1-dimethyl-2,3,4,5-tetraphenylstannole and phenylboron dichloride.[2] Boroles can be used to form ferrocene-like sandwich compounds.[3]
See also
References
- ^ Alan R. Katritzky, ed. (1993), Advances in Heterocyclic Chemistry, vol. 56, Academic Press, p. 375, ISBN 978-0-12-020756-5, retrieved 2010-03-13
- ^ Francis Gordon Albert Stone, Robert West, ed. (1996), Advances in Heterocyclic Chemistry, vol. 39, Academic Press, p. 380, ISBN 978-0-12-031139-2, retrieved 2010-03-13
- ^ Alan R. Katritzky, ed. (2001), Advances in Heterocyclic Chemistry, vol. 79, Academic Press, pp. 169–170, ISBN 978-0-12-020779-4, retrieved 2010-03-13