Stannole Explained

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

• Organotin chemistry

Notes and References

1. Dubac. Jacques. Laporterie. Andre. Manuel. Georges. Group 14 metalloles. 1. Synthesis, organic chemistry, and physicochemical data. Chemical Reviews. 90. 215–263. 1990. 10.1021/cr00099a008.
2. Web site: DTXSID70781612. pubchem.ncbi.nlm.nih.gov. en.
3. Ashe. Arthur J.. Mahmoud. Samir.. 1,4-Dilithio-1,3-butadienes. Organometallics. 7. 1878. 1988. 10.1021/om00098a034. 8.
4. Book: J.I.G. Cadogan . S.V. Ley . G. Pattenden . R.A. Raphael . C.W. Rees . Charles Rees. 1996. Dictionary of Organic Compounds. 6. 3. Chapman & Hall. 4219. 978-0-412-54090-5. 2010-03-04.
5. Book: Davies , A.G. . 2004. Organotin Chemistry. 2. Wiley-VCH. 129. 978-3-527-31023-4. 2010-03-04.