Stannole

{{Short description|Organotin compound}} {{Chembox |ImageFileL1 = Stannole.svg |ImageFileL1_Ref = {{Chemboximage|correct|??}} |ImageSizeL1 = 100 |ImageNameL1 = Skeletal formula of stannole |ImageFileR1 = Stannole-Spartan-MP2-3D-balls.png |ImageSizeR1 = 120 |PIN = 1''H''-Stannole |OtherNames = |Section1={{Chembox Identifiers |CASNo = 288-07-3 |CASNo_Ref = {{cascite|changed|??}} |PubChem = 71357546 |SMILES = [SnH2]1C=CC=C1 |StdInChI = InChI=1S/C4H4.Sn.2H/c1-3-4-2;;;/h1-4H;;; |StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey = UCLKYZNUCJCVMQ-UHFFFAOYSA-N |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |ChemSpiderID = 57535729 }} |Section2={{Chembox Properties | C=4 | H=6 | Sn=1 }} }}

'''Stannole''' is an organotin compound with the formula (CH)₄SnH₂. It is classified as a metallole, i.e. an unsaturated five-membered ring containing a heteroatom. It is a structural analog of cyclopentadiene, with tin replacing the saturated carbon atom. Substituted derivatives, which have been synthesized, are also called stannoles.<ref>{{cite journal|last1 = Dubac|first1 = Jacques|last2 = Laporterie|first2 = Andre|last3 = Manuel|first3 = Georges|title = Group 14 metalloles. 1. Synthesis, organic chemistry, and physicochemical data|journal = Chemical Reviews|volume = 90|pages = 215–263|year = 1990|doi = 10.1021/cr00099a008}}</ref>

==Examples== 1,1-Dibutylstannole is a pale yellow oil prepared from 1,4-dilithio-1,3-butadiene and dibutyltin dichloride.<ref>{{cite journal|last1 = Ashe|first1 = Arthur J.|last2 = Mahmoud|first2 = Samir.|title = 1,4-Dilithio-1,3-butadienes|journal = Organometallics|volume = 7|pages = 1878|year = 1988|doi = 10.1021/om00098a034|issue = 8}}</ref> :1,1-dibutylstannole

1,1-Dimethyl-2,3,4,5-tetraphenyl-1''H''-stannole, for example, can be formed by the displacement reaction of 1,4-dilithio-1,2,3,4-tetraphenyl-1,3-butadiene and dimethyltin dichloride.<ref name = "dict"> {{Cite book |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 | publication-place = | publisher = Chapman & Hall | pages = 4219 | isbn =978-0-412-54090-5 | url= https://books.google.com/books?id=C3Uo1co4Wv0C&pg=PA4219 | accessdate = 2010-03-04 }}</ref>

Palladium and cobalt catalyze a [2+2+1] cycloaddition between two acetylene molecules and a stannylene SnR₂ to give the corresponding stannole.<ref name = "ot"> {{Cite book | last =Davies | first =A.G. | year = 2004 | title =Organotin Chemistry | edition =2 | publication-place = | publisher = Wiley-VCH | pages = 129 | isbn =978-3-527-31023-4 | url= {{GBUrl|id=sIyUnsahhYAC|p=129}} | accessdate = 2010-03-04 }} </ref>

==Related compounds==<!--super-esoteric, maybe rm?--> 1λ²-Stannole has formula C₄H₄Sn, with no hydrogen on the tin atom, which is in the +2 oxidation state.<ref>{{cite web|title=DTXSID70781612|url=https://pubchem.ncbi.nlm.nih.gov/compound/57458877|website=pubchem.ncbi.nlm.nih.gov|language=en}}</ref>

==See also== *Organotin chemistry

==References== {{Reflist}}

Category:Tin heterocycles Category:Metalloles Category:Tin(IV) compounds