Tributyltin hydride: Difference between revisions

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 397447183

| ImageFileL1 = Tributyltin hydride.svg

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageNameL1 = Skeletal formula of tributyltin with one explicit hydrogen added

| ImageFileR1 = Tributyltin hydride.png

| ImageFileR1_Ref = {{chemboximage|correct|??}}

| ImageNameR1 = Spacefill model of tributyltin

| ImageFile2 = Tributyltin-hydride-3D-balls.png

| ImageFile2_Ref = {{chemboximage|correct|??}}

| ImageName2 = Ball and stick model of tributyltin

| SystematicName = Tributylstannane<ref>{{Cite web|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5948|title = SnBu3H - PubChem Public Chemical Database|work = The PubChem Project|location = USA|publisher = National Center for Biotechnology Information}}</ref>

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4XDX163P3D

| PubChem = 5948

| ChemSpiderID = 5734

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| EINECS = 211-704-4

| MeSHName = Tributyltin

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 27086

| Beilstein = 3587329

| Gmelin = 4258

| SMILES = CCCC[SnH](CCCC)CCCC

| StdInChI = 1S/3C4H9.Sn.H/c3*1-3-4-2;;/h3*1,3-4H2,2H3;;

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = DBGVGMSCBYYSLD-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

}}

|Section2={{Chembox Properties

| Formula = {{Chem|SnC|12|H|28}}

| MolarMass = 291.06 g mol⁻¹

| Density = 1.082 g cm⁻³

| BoilingPtC = 80

| BoilingPt_notes = at 50&nbsp;Pa

| Solubility = Slowly reacts{{Citation needed|date=September 2012}}

}}

'''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 compound is produced by reduction of [[tributyltin oxide]] with polymethylhydrosiloxane:<ref>{{cite journal|title=Application of Fluoride-Catalyzed Silane Reductions of Tin Halides to the in Situ Preparation of Vinylstannanes|first1=Robert E. |last1=Maleczka|first2=Lamont R. |last2=Terrell|first3=Damon H. |last3=Clark|first4=Susan L.|last4=Whitehead|first5=William P.|last5=Gallagher|first6=Ina |last6=Terstiege|journal=J. Org. Chem.|year=1999|volume=64|issue=16 |pages=5958–5965|doi=10.1021/jo990491+}}</ref><ref>{{cite journal|title=α-D-Ribo-hexofuranose, 3-deoxy-1,2:5,6-bis-''O''-(1-methylethylidene)|first1=J.|last1=Tormo|last2=Fu|first2=G. C.|journal=Org. Synth.|volume=78|page=239|year=2002|doi=10.15227/orgsyn.078.0239}}</ref>

: 2 "[MeSi(H)O]_n" + (Bu₃Sn)₂O → "[MeSi(OH)O]_n" + 2 Bu₃SnH

The hydride is a distillable liquid that is mildly sensitive to air, decomposing to (Bu₃Sn)₂O. Its [[IR spectrum]] exhibits a strong band at 1814&nbsp;cm⁻¹ for ''ν''_Sn−H.

==Applications==

{{See also|Barton–McCombie deoxygenation}}

It is a specialized reagent in [[organic synthesis]]. Combined with [[azobisisobutyronitrile]] (AIBN) or by irradiation with light, tributyltin hydride converts organic halides (and related groups) to the corresponding hydrocarbon. This process occurs via a radical chain mechanism involving the radical Bu₃Sn^•.<ref name="Clayden">[http://www.oup.com/uk/catalogue/?ci=9780198503460 OUP catalogue page], J. Clayden, N. Greeves, S. Warren and P. Wothers, in ''Organic Chemistry'', 2000, OUP, Oxford, ch. 39, pp. 1040-1041.</ref><ref>T. V. (Babu) RajanBabu, Philip C. Bulman Page, Benjamin R. Buckley, "Tri-''n''-butylstannane" Encyclopedia of Reagents for Organic Synthesis

2004, John Wiley & Sons. {{doi|10.1002/047084289X.rt181.pub2}}</ref> The radical abstracts a H^• from another equivalent of tributyltin hydride, propagating the chain. Tributyltin hydride's utility as a H^• donor can be attributed to its relatively weak bond strength (78 kcal/mol).<ref>Laarhoven, L. J. J.; Mulder, P.; Wayner, D.D. M. "Determination of Bond Dissociation Enthalpies in Solution by Photoacoustic Calorimetry" Acc. Chem. Res. 1999, 32, 342 {{doi|10.1021/ar9703443}}</ref>

It is the reagent of choice for [[hydrostannylation]] reactions:<ref>{{cite journal|doi=10.1021/cr9902695|pmid=11749320|title=Metal-Catalyzed Hydrostannations|journal=Chemical Reviews|volume=100|issue=8|pages=3257–3282|year=2000|last1=Smith|first1=Nicholas D.|last2=Mancuso|first2=John|last3=Lautens|first3=Mark}}</ref>

:RC₂R′ + HSnBu₃ → RC(H)=C(SnBu₃)R′

* [[Trimethylsilyl]]

== References ==

{{Reflist}}

==Further reading==

* Hayashi, K.; Iyoda, J.; Shiihara, I. "Reaction of organotin oxides, alkoxides and acyloxides with organosilicon hydrides. New preparative method of organotin hydrides " J. Organomet. Chem. 1967, 10, 81. {{doi|10.1016/S0022-328X(00)81719-2}}

[[Category:Radical initiators]]

[[Category:Metal hydrides]]

[[Category:Tin(IV) compounds]]

[[Category:Butyl compounds]]