Stibole

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.

Stibole

Names
Preferred IUPAC name 1H-Stibole
Identifiers
CAS Number	288-04-0 N
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;; Y Key: BTXJFXLZTKRZGF-UHFFFAOYSA-N Y
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

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

• Organoantimony chemistry