# Stibole

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> Markdown URL: https://mediated.wiki/source/Stibole.md
> Source: https://en.wikipedia.org/wiki/Stibole
> Source revision: 1342584386
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{{Chembox
| ImageFileL1 = stibole.png
|  ImageFileL1_Ref = {{Chemboximage|correct|??}}
|  ImageSizeL1 = 80
|  ImageAltL1 = Structural formula of stibole with an explicit hydrogen
| ImageFileR1 = Stibole-3D-balls.png
|  ImageSizeR1 = 150
|  ImageAltR1 = Ball-and-stick model of the stibole molecule
| PIN = 1''H''-Stibole
| Section1 = {{Chembox Identifiers
|  CASNo = 288-04-0
|   CASNo_Ref = {{cascite|changed|??}}
|  SMILES = [SbH]1C=CC=C1
|  StdInChI = 1S/C4H4.Sb.H/c1-3-4-2;;/h1-4H;;
|   StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|  StdInChIKey = BTXJFXLZTKRZGF-UHFFFAOYSA-N
|   StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|  ChemSpiderID = 58539793
|  PubChem = 91869492
}}
| Section2 = {{Chembox Properties
|  C = 4
|  H = 5
|  Sb = 1
}}
|Section8={{Chembox Related
| OtherCompounds = [Pyrrole](/source/Pyrrole), [phosphole](/source/phosphole), [arsole](/source/arsole), [bismole](/source/bismole)}}
}}

'''Stibole''' is a [heterocyclic](/source/heterocyclic) [organic compound](/source/organic_compound), a five-membered ring with the [formula](/source/chemical_formula) [C](/source/carbon)<sub>4</sub>[H](/source/hydrogen)<sub>4</sub>[Sb](/source/antimony)H. It is classified as a [metallole](/source/metallole). It can be viewed as a [structural analog](/source/structural_analog) of [pyrrole](/source/pyrrole), with antimony replacing the [nitrogen](/source/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](/source/1%2C2%2C3%2C4-Tetraphenylbutadiene) and phenylantimony dichloride by a [salt metathesis reaction](/source/salt_metathesis_reaction):<ref>{{cite journal |doi=10.1021/ja01504a021 |title=Novel Heterocyclopentadienes. II |date=1960 |last1=Leavitt |first1=F. C. |last2=Manuel |first2=T. A. |last3=Johnson |first3=F. |last4=Matternas |first4=L. U. |last5=Lehman |first5=D. S. |journal=Journal of the American Chemical Society |volume=82 |issue=19 |pages=5099–5102 |bibcode=1960JAChS..82.5099L }}</ref>
:{{chem2| LiCPh\dCPh\sCPh\dCPhLi +  PhSbCl2  ->  Ph4C4SbPh  +  2 LiCl}} (Ph = [C<sub>6</sub>H<sub>5</sub>](/source/phenyl))
Even simpler than the above, 1-phenylstibole can be prepared analgously from 1,4-dilithiobutadiene.  It is yellow oil that [resin](/source/resin)ifies at room temperature.<ref>{{cite journal |last1=Ashe |first1=Arthur J. |last2=Drone |first2=Frederick J. |title=Synthesis of 1-phenylarsole and 1-phenylstibole |journal=Organometallics |date=1985 |volume=4 |issue=8 |pages=1478–1480 |doi=10.1021/om00127a038}}</ref>

2,5-Dimethyl-1-phenyl-1''H''-stibole, for example, can be formed by the reaction of 1,1-dibutyl-2,5-dimethyl[stannole](/source/stannole) and dichlorophenylstibine.<ref name = "dict">
{{Citation
 | editor1=J.I.G. Cadogan |editor2=S.V. Ley |editor3=G. Pattenden |editor4=R.A. Raphael |editor5=C.W. Rees |editor-link5 = Charles Rees
 | year = 1996
 | title =Dictionary of Organic Compounds
 | edition =6
 | volume =3
 | series =
 | publication-place =
 | place =
 | publisher = Chapman & Hall
 | pages = 2710
 | id =
 | isbn =978-0-412-54090-5
 | doi =
 | oclc =
 |  url= https://books.google.com/books?id=C3Uo1co4Wv0C&pg=PA2710
 | accessdate = 2010-03-04
}}
</ref> 

==Derivatives==
Stibolides ({{chem2|C4R4Sb-}}) form [half-sandwich compound](/source/half-sandwich_compound)s.<ref name = "comp">
{{Citation
 |editor1=A.R. Katritzky |editor-link1=Alan R. Katritzky |editor2=Otto Meth-Cohn |editor3=C.W. Rees |editor-link3=Charles Rees
 | year = 1995
 | title =Comprehensive Organic Functional Group Transformations
 | edition =
 | volume =4
 | series =
 | publication-place =
 | place =
 | publisher = Elsevier
 | pages = 1038–1040
 | id =
 | isbn =978-0-08-042325-8
 | doi =
 | oclc =
 |  url= https://books.google.com/books?id=0RQEsfYCuBcC&pg=PA1038
 | accessdate = 2010-03-04
}}
</ref>

==See also==
*[Organoantimony chemistry](/source/Organoantimony_chemistry)

==References==
{{Reflist}}

Category:Antimony heterocycles
Category:Metalloles
Category:Hypothetical chemical compounds

{{Heterocyclic-stub}}
{{theoretical-chem-stub}}

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Adapted from the Wikipedia article [Stibole](https://en.wikipedia.org/wiki/Stibole) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Stibole?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.