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Borole

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Borole
Names
IUPAC name 1H-Borole
Identifiers
CAS Number
3D model (JSmol)
CompTox Dashboard (EPA)
SMILES
  • C1=CC=CB1
Properties
Chemical formula C4H5B
Molar mass 63.89 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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 Rule cannot be strictly applied to borole, it is considered to be anti-aromatic.

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. Boroles can be used to form ferrocene-like sandwich compounds.

See also

References

  1. Alan R. Katritzky, ed. (1993), Advances in Heterocyclic Chemistry, vol. 56, Academic Press, p. 375, ISBN 9780120207565, retrieved 2010-03-13
  2. Francis Gordon Albert Stone, Robert West, ed. (1996), Advances in Heterocyclic Chemistry, vol. 39, Academic Press, p. 380, ISBN 9780120311392, retrieved 2010-03-13
  3. Alan R. Katritzky, ed. (2001), Advances in Heterocyclic Chemistry, vol. 79, Academic Press, pp. 169–170, ISBN 9780120207794, retrieved 2010-03-13
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