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Skeletal formula of stannole Stannole-Spartan-MP2-3D-balls.png
CAS number 288-07-3 N
Jmol-3D images Image 1
Image 2
Molecular formula C4H6Sn
Molar mass 172.80 g mol−1
Except where noted otherwise, 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]


1,1-Dibutylstannole is a pale yellow oil prepared from 1,4-dilithio-1,3-butadiene and dibutyltin dichloride [2]



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[edit]


  1. ^ 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. 
  2. ^ Ashe, Arthur J.; Mahmoud, Samir. (1988). "1,4-Dilithio-1,3-butadienes". Organometallics 7 (8): 1878. doi:10.1021/om00098a034. 
  3. ^ J.I.G. Cadogan, S.V. Ley, G. Pattenden, R.A. Raphael, C.W. Rees, ed. (1996). Dictionary of Organic Compounds 3 (6 ed.). Chapman & Hall. p. 4219. ISBN 978-0-412-54090-5. Retrieved 2010-03-04. 
  4. ^ Davies, A.G. (2004). Organotin Chemistry (2 ed.). Wiley-VCH. p. 129. ISBN 978-3-527-31023-4. Retrieved 2010-03-04.