Borole

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Borole
Skeletal formula of borole
Ball-and-stick model of the borole molecule
Space-filling model of the borole molecule
Names
IUPAC name
1H-Borole
Identifiers
3D model (Jmol)
ChemSpider
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).
N verify (what is YesYN ?)
Infobox references

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 a 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[edit]

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]

Pentaphenylborole-synthesis-1969-2D-skeletal.png

See also[edit]

References[edit]

  1. ^ Alan R. Katritzky, ed. (1993), Advances in Heterocyclic Chemistry, 56, Academic Press, p. 375, ISBN 978-0-12-020756-5, retrieved 2010-03-13 
  2. ^ Francis Gordon Albert Stone, Robert West, ed. (1996), Advances in Heterocyclic Chemistry, 39, Academic Press, p. 380, ISBN 978-0-12-031139-2, retrieved 2010-03-13 
  3. ^ Alan R. Katritzky, ed. (2001), Advances in Heterocyclic Chemistry, 79, Academic Press, pp. 169–170, ISBN 978-0-12-020779-4, retrieved 2010-03-13