Tributyltin hydride

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| verifiedrevid = 397447183

| ImageFileL1 = Tributyltin hydride.svg

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

| ImageFileR1 = Tributyltin hydride.png

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| ImageNameR1 = Spacefill model of tributyltin

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

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| ImageName2 = Ball and stick model of tributyltin

| SystematicName = Tributylstannane{{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}}

|Section1={{Chembox Identifiers

| CASNo = 688-73-3

| 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}}

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|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 Pa

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

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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:{{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+}}{{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}}

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

It can also be synthesized by a reduction of tributyltin chloride with lithium aluminium hydride.

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 cm⁻¹ for ν_Sn−H.

Applications

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^•.[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.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}} 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).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}}

It is the reagent of choice for hydrostannylation reactions:{{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}}

:RC₂R′ + HSnBu₃ → RC(H)=C(SnBu₃)R′

Tributyltin hydride

Synthesis and characterization

Applications

See also

References

Further reading