Stannole

Quality 0.50 · 2 views · Updated 2 months ago

Organotin compound

title: "Stannole" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["tin-heterocycles", "metalloles", "tin(iv)-compounds"] description: "Organotin compound" topic_path: "general/tin-heterocycles" source: "https://en.wikipedia.org/wiki/Stannole" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Organotin compound ::

|ImageFileL1 = Stannole.svg |ImageFileL1_Ref = |ImageSizeL1 = 100 |ImageNameL1 = Skeletal formula of stannole |ImageFileR1 = Stannole-Spartan-MP2-3D-balls.png |ImageSizeR1 = 120 |PIN = 1H-Stannole |OtherNames = |Section1={{Chembox Identifiers |CASNo = 288-07-3 |CASNo_Ref = |PubChem = 71357546 |SMILES = [SnH2]1C=CC=C1 |StdInChI = InChI=1S/C4H4.Sn.2H/c1-3-4-2;;;/h1-4H;;; |StdInChI_Ref = |StdInChIKey = UCLKYZNUCJCVMQ-UHFFFAOYSA-N |StdInChIKey_Ref = |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.

Examples

1,1-Dibutylstannole is a pale yellow oil prepared from 1,4-dilithio-1,3-butadiene and dibutyltin dichloride. :[[File:1,1-dibutylstannole.svg|1,1-dibutylstannole]]

1,1-Dimethyl-2,3,4,5-tetraphenyl-1H-stannole, for example, can be formed by the displacement reaction of 1,4-dilithio-1,2,3,4-tetraphenyl-1,3-butadiene and . |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

Palladium and cobalt catalyze a [2+2+1] cycloaddition between two acetylene molecules and a stannylene SnR2 to give the corresponding stannole. | 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= | accessdate = 2010-03-04

Related compounds==

1λ2-Stannole has formula C4H4Sn, with no hydrogen on the tin atom, which is in the +2 oxidation state.

References

References

  1. (1990). "Group 14 metalloles. 1. Synthesis, organic chemistry, and physicochemical data". Chemical Reviews.
  2. (1988). "1,4-Dilithio-1,3-butadienes". Organometallics.
  3. "DTXSID70781612".

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

tin-heterocyclesmetallolestin(iv)-compounds