Stannole

Stannole

Skeletal formula of stannole 120px
Names
IUPAC name 1H-Stannole
Identifiers
CAS Number	288-07-3 N
Jmol 3D model	Interactive image Interactive image
InChI InChI=1S/C4H4.Sn/c1-3-4-2;/h1-4H; Y Key: HVWGTGTZCBPIOH-UHFFFAOYSA-N Y
SMILES [SnH2]1C=CC=C1 C1=CC=CSn1
Properties
Chemical formula	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.

Examples

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

1,1-dibutylstannole

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. 1,1-Disubstituted stannoles can be formed in the [2+2+1] cycloaddition reaction of two acetylene molecules with an organotin molecule SnR₂.

See also

• Organotin chemistry