Stannole
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| Names | |||
|---|---|---|---|
| IUPAC name
1H-Stannole | |||
| Identifiers | |||
288-07-3  | |||
| 3D model (Jmol) | Interactive image Interactive image | ||
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| Properties | |||
| C4H6Sn | |||
| Molar mass | 172.80 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 pyrrole, with tin replacing the nitrogen. Substituted derivatives, which have been synthesized, are also called stannoles.[1]
Examples
1,1-Dibutylstannole is a pale yellow oil prepared from 1,4-dilithio-1,3-butadiene and dibutyltin dichloride [2]
Reactions
1,1-Dimethyl-2,3,4,5-tetraphenyl-1H-stannole, for example, can be formed by the reaction of 1,4-dilithio-1,2,3,4-tetraphenyl-1,3-butadiene and dimethyltin dichloride.[3] 1,1-Disubstituted stannoles can be formed in the [2+2+1] cycloaddition reaction of two acetylene molecules with an organotin molecule SnR2.[4]
See also
References
- ↑ Dubac, Jacques; Laporterie, Andre; Manuel, Georges (1990). "Group 14 metalloles. 1. Synthesis, organic chemistry, and physicochemical data". Chemical Reviews. 90: 215. doi:10.1021/cr00099a008.
- ↑ Ashe, Arthur J.; Mahmoud, Samir. (1988). "1,4-Dilithio-1,3-butadienes". Organometallics. 7 (8): 1878. doi:10.1021/om00098a034.
- ↑ J.I.G. Cadogan; S.V. Ley; G. Pattenden; R.A. Raphael; C.W. Rees, eds. (1996). Dictionary of Organic Compounds. 3 (6 ed.). Chapman & Hall. p. 4219. ISBN 978-0-412-54090-5. Retrieved 2010-03-04.
- ↑ Davies, A.G. (2004). Organotin Chemistry (2 ed.). Wiley-VCH. p. 129. ISBN 978-3-527-31023-4. Retrieved 2010-03-04.
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