Vinyl tributyltin is an organotin compound with the formula Bu₃SnCH=CH₂ (Bu =

butyl In organic chemistry, butyl is a four- carbon alkyl radical or substituent group with general chemical formula , derived from either of the two isomers (''n''-butane and isobutane) of butane. The isomer ''n''-butane can connect in two ways, gi ...

). It is a white, air-stable solid. It is used as a source of vinyl anion equivalent in

Stille coupling The Stille reaction is a chemical reaction widely used in organic synthesis. The reaction involves the coupling of two organic groups, one of which is carried as an organotin compound (also known as organostannanes). A variety of organic electroph ...

reactions. As a source of vinyltin reagents, early work used vinyl trimethyltin, but trimethyltin compounds are avoided nowadays owing to their toxicity.

Preparation

The compound is prepared by the reaction of vinylmagnesium bromide with

tributyltin chloride Tributyltin chloride is an organotin compound with the formula ( C4H9)3SnCl. It is a colorless liquid that is soluble in organic solvents. Preparation and reactions The compound is prepared by a redistribution reaction by combining stannic ch ...

. It can be synthesized in the laboratory by

hydrostannylation In chemistry, hydrostannylation is the insertion of unsaturated substrates into an Sn-H bond. The reaction occurs under free-radical conditions, but the stereochemistry and regiochemistry are often complex. The reaction gained synthetic importance ...

of acetylene with

tributyltin hydride Tributyltin hydride is an organotin compound with the formula (C4H9)3SnH. It is a colorless liquid that is soluble in organic solvents. The compound is used as a source of hydrogen atoms in organic synthesis. Synthesis and characterization The c ...

. It is commercially available.

References

{{Reflist Organotin compounds Vinyl compounds Tin(IV) compounds