Vinyl tributyltin is an
organotin compound
Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide (), discovered ...
with the formula Bu
3SnCH=CH
2 (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, giv ...
). 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 electrop ...
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 chlo ...
.
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
Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...
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