View source for 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 [[chemical formula|formula]] ([[carbon|C]][[hydrogen|H]])<sub>4</sub>[[tin|Sn]]H<sub>2</sub>. 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>
1λ<sup>2</sup>-Stannole has formula C<sub>4</sub>H<sub>4</sub>Sn, 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>
==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>
:[[File:1,1-dibutylstannole.svg|1,1-dibutylstannole]]
==Reactions==
1,1-Dimethyl-2,3,4,5-tetraphenyl-1''H''-stannole, for example, can be formed by the [[double displacement|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>
1,1-Disubstituted stannoles can be formed in the [2+2+1] [[cycloaddition reaction]] of two [[acetylene]] molecules with an [[organotin]] molecule SnR<sub>2</sub>.<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= https://books.google.com/books?id=sIyUnsahhYAC&pg=PA129
| accessdate = 2010-03-04
}}
</ref>
==See also==
*[[Organotin chemistry]]
==References==
{{Reflist}}
[[Category:Tin heterocycles]]
[[Category:Metalloles]]
[[Category:Tin(IV) compounds]]