Stibole

Stibole
Names
Preferred IUPAC name
1H-Stibole
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C4H4.Sb.H/c1-3-4-2;;/h1-4H;; Y
    Key: BTXJFXLZTKRZGF-UHFFFAOYSA-N Y
  • [SbH]1C=CC=C1
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).
Infobox references

Stibole is a theoretical 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 is very rare, but many substituted derivatives have been synthesized. They are called stiboles.

Reactions

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)

2,5-Dimethyl-1-phenyl-1H-stibole, for example, can be formed by the reaction of 1,1-dibutyl-2,5-dimethylstannole and dichlorophenylstibine.[2] Stiboles can be used to form ferrocene-like sandwich compounds.[3]

See also

References

  1. 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.
  2. 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
  3. 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