{{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, phosphole, arsole, bismole}} }}
'''Stibole''' is a heterocyclic organic compound, a five-membered ring with the formula C<sub>4</sub>H<sub>4</sub>SbH. 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:<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>) Even simpler than the above, 1-phenylstibole can be prepared analgously from 1,4-dilithiobutadiene. It is yellow oil that resinifies 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-dimethylstannole 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 compounds.<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
==References== {{Reflist}}
Category:Antimony heterocycles Category:Metalloles Category:Hypothetical chemical compounds
{{Heterocyclic-stub}} {{theoretical-chem-stub}}