Stibole

Stibole
Names
	Preferred IUPAC name 1H-Stibole
Identifiers
CAS Number	288-04-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	58539793;
PubChem CID	91869492;
CompTox Dashboard (EPA)	DTXSID101029323 ;
	InChI InChI=1S/C4H4.Sb.H/c1-3-4-2;;/h1-4H;; Key: BTXJFXLZTKRZGF-UHFFFAOYSA-N ;
	SMILES [SbH]1C=CC=C1;
Properties
Chemical formula	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 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

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

Stibolides (C₄R₄Sb⁻) form half-sandwich compounds.^[4]

References

^ 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

[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] Ashe, Arthur J.; Drone, Frederick J. (1985). "Synthesis of 1-phenylarsole and 1-phenylstibole". Organometallics. 4 (8): 1478–1480. doi:10.1021/om00127a038.

[dict-3] 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

[comp-4] 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

[1]

[2]

[3]

[4]

Preparation

Derivatives

See also

References