Stannole

Stannole
Skeletal formula of stannole
Names
	Preferred IUPAC name 1H-Stannole
Identifiers
CAS Number	288-07-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	57535729;
PubChem CID	71357546;
CompTox Dashboard (EPA)	DTXSID70781612 ;
	InChI InChI=1S/C4H4.Sn.2H/c1-3-4-2;;;/h1-4H;;; Key: UCLKYZNUCJCVMQ-UHFFFAOYSA-N ;
	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 (C H)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-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]

^ Dubac, Jacques; Laporterie, Andre; Manuel, Georges (1990). "Group 14 metalloles. 1. Synthesis, organic chemistry, and physicochemical data". Chemical Reviews. 90: 215–263. doi:10.1021/cr00099a008.
^ "DTXSID70781612". pubchem.ncbi.nlm.nih.gov.
^ Ashe, Arthur J.; Mahmoud, Samir. (1988). "1,4-Dilithio-1,3-butadienes". Organometallics. 7 (8): 1878. doi:10.1021/om00098a034.
^ 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.
^ Davies, A.G. (2004). Organotin Chemistry (2 ed.). Wiley-VCH. p. 129. ISBN 978-3-527-31023-4. Retrieved 2010-03-04.