Stannole

Stannole

Skeletal formula of stannole
Names
Preferred IUPAC name 1H-Stannole
Identifiers
CAS Number	288-07-3 N
3D model (JSmol)	Interactive image
ChemSpider	57535729
ECHA InfoCard
E number
PubChem CID	71357546
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C4H4.Sn.2H/c1-3-4-2;;;/h1-4H;;; checkY Key: UCLKYZNUCJCVMQ-UHFFFAOYSA-N checkY
SMILES [SnH2]1C=CC=C1
Properties
Chemical formula	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.

Examples

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

1,1-dibutylstannole

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.

Palladium and cobalt catalyze a [2+2+1] cycloaddition between two acetylene molecules and a stannylene SnR₂ to give the corresponding stannole.

Related compounds

1λ²-Stannole has formula C₄H₄Sn, with no hydrogen on the tin atom, which is in the +2 oxidation state.

See also

• Organotin chemistry