Stannole
Skeletal formula of stannole
Skeletal formula of stannole
Names
Preferred IUPAC name
1H-Stannole
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C4H4.Sn.2H/c1-3-4-2;;;/h1-4H;;; checkY
    Key: UCLKYZNUCJCVMQ-UHFFFAOYSA-N checkY
  • [SnH2]1C=CC=C1
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]

1,1-dibutylstannole

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

  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. ↑ "DTXSID70781612". pubchem.ncbi.nlm.nih.gov.
  3. ↑ Ashe, Arthur J.; Mahmoud, Samir. (1988). "1,4-Dilithio-1,3-butadienes". Organometallics. 7 (8): 1878. doi:10.1021/om00098a034.
  4. ↑ J.I.G. Cadogan; S.V. Ley; G. Pattenden; R.A. Raphael; C.W. Rees, eds. (1996). Dictionary of Organic Compounds. Vol. 3 (6 ed.). Chapman & Hall. p. 4219. ISBN 978-0-412-54090-5. Retrieved 2010-03-04.
  5. ↑ 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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