Chemistry:Stannole
| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name
1H-Stannole | |||
| Identifiers | |||
3D model (JSmol)
|
|||
| ChemSpider | |||
PubChem CID
|
|||
| |||
| |||
| Properties | |||
| C4H6Sn | |||
| Molar mass | 172.802 g·mol−1 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
| Infobox references | |||
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.[1]
1λ2-Stannole has formula C4H4Sn, with no hydrogen on the tin atom, which is in the +2 oxidation state.[2]
Examples
1,1-Dibutylstannole is a pale yellow oil prepared from 1,4-dilithio-1,3-butadiene and dibutyltin dichloride.[3]
Reactions
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 dimethyltin dichloride.[4] 1,1-Disubstituted stannoles can be formed in the [2+2+1] cycloaddition reaction of two acetylene molecules with an organotin molecule SnR2.[5]
See also
References
- ↑ Dubac, Jacques; Laporterie, Andre; Manuel, Georges (1990). "Group 14 metalloles. 1. Synthesis, organic chemistry, and physicochemical data". Chemical Reviews 90: 215–263. doi:10.1021/cr00099a008.
- ↑ "DTXSID70781612" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/57458877.
- ↑ Ashe, Arthur J.; Mahmoud, Samir. (1988). "1,4-Dilithio-1,3-butadienes". Organometallics 7 (8): 1878. doi:10.1021/om00098a034.
- ↑ Dictionary of Organic Compounds. 3 (6 ed.). Chapman & Hall. 1996. pp. 4219. ISBN 978-0-412-54090-5. https://books.google.com/books?id=C3Uo1co4Wv0C&pg=PA4219. Retrieved 2010-03-04.
- ↑ Davies, A.G. (2004). Organotin Chemistry (2 ed.). Wiley-VCH. pp. 129. ISBN 978-3-527-31023-4. https://books.google.com/books?id=sIyUnsahhYAC&pg=PA129. Retrieved 2010-03-04.
 |  |
