Vinyl tributyltin
{{Chembox
| ImageFile = Bu3SnCH=CH2.svg
| ImageSize =
| ImageAlt =
| PIN = Tributyl(ethenyl)stannane
| OtherNames = Tributylvinyltin, Tributylvinylstannane
| Section1 = {{Chembox Identifiers
| CASNo = 7486-35-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2FA6XM467X
| PubChem = 81998
| ChemSpiderID = 74003
| EC_number = 231-291-4
| DTXSID = DTXSID40225836
| StdInChI=1S/3C4H9.C2H3.Sn/c3*1-3-4-2;1-2;/h3*1,3-4H2,2H3;1H,2H2;
| StdInChIKey = QIWRFOJWQSSRJZ-UHFFFAOYSA-N
| SMILES = CCCC[Sn](CCCC)(CCCC)C=C
}}
| Section2 = {{Chembox Properties
| C=14|H=30|Sn=1
| MolarMass =
| Appearance = colorless oil
| Density = 1.081 g/cm3
| BoilingPtC = 253-254
| MeltingPtC = 95
| BoilingPt_notes = 1.5 Torr
| Solubility = }}
| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|226|301|312|315|319|372|410}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|260|264|270|273|280|301+310|302+352|303+361+353|305+351+338|312|314|321|322|330|332+313|337+313|362|363|370+378|391|403+235|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
Vinyl tributyltin is an organotin compound with the formula Bu3SnCH=CH2 (Bu = butyl). It is a white, air-stable solid. It is used as a source of vinyl anion equivalent in Stille coupling reactions.{{cite journal|doi=10.1021/ja00025a025|title=Large Rate Accelerations in the Stille Reaction with Tri-2-furylphosphine and Triphenylarsine as Palladium Ligands: Mechanistic and synthetic implications|journal=Journal of the American Chemical Society|volume=113|pages=9585–9595|year=1991|last1=Farina|first1=Vittorio|last2=Krishnan|first2=Bala|issue=25}}{{cite journal|doi=10.1021/ja020012f|pmid=12033863|title=Pd/P(t-Bu)3: A Mild and General Catalyst for Stille Reactions of Aryl Chlorides and Aryl Bromides|journal=Journal of the American Chemical Society|volume=124|pages=6343–6348|year=2002|last1=Littke|first1=Adam F.|last2=Schwarz|first2=Lothar|last3=Fu|first3=Gregory C.|issue=22}} As a source of vinyltin reagents, early work used vinyl trimethyltin,{{cite journal|doi=10.15227/orgsyn.068.0116|title=Palladium-Catalyzed Coupling of Vinyl Triflates With Organostannanes: 4-tert-Butyl-1-vinylcyclohexene and 1-(4-tert-Butylcyclohexen-1-yl)-2-propen-1-one|first1=William J. |last1=Scott|first2=G. T. |last2=Crisp|first3=J. K.|last3=Stille|
journal=Organic Syntheses|volume=68|pages=116|year=1990}} but trimethyltin compounds are avoided nowadays owing to their toxicity.
Preparation
The compound is prepared by the reaction of vinylmagnesium bromide with tributyltin chloride.{{cite journal|title=Di-n-butyldivinyltin|author=Dietmar Seyferth|journal=Org. Synth. |year=1959|volume=39|page=10|doi=10.15227/orgsyn.039.0010}} It can be synthesized in the laboratory by hydrostannylation of acetylene with tributyltin hydride. It is commercially available.