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| verifiedrevid = 308536910 |
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| Name = Tributyltin hydride |
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| verifiedrevid = 397447183 |
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| ImageFile = Tributyltin hydride.svg |
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| ImageFileL1 = Tributyltin-hydride-3D-balls.png |
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| ImageFileL1 = Tributyltin hydride.svg |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFileR1 = Tributyltin.png |
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| ImageNameL1 = Skeletal formula of tributyltin with one explicit hydrogen added |
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| ImageName1 = Tributyltin hydride |
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| ImageFileR1 = Tributyltin hydride.png |
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| IUPACName = Tributylstannane |
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| ImageNameR1 = Spacefill model of tributyltin |
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| Section1 = {{Chembox Identifiers |
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| ImageFile2 = Tributyltin-hydride-3D-balls.png |
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| CASNo_Ref = {{cascite}} |
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| ImageFile2_Ref = {{chemboximage|correct|??}} |
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| ImageName2 = Ball and stick model of tributyltin |
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| 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> |
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|Section1={{Chembox Identifiers |
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| CASNo = 688-73-3 |
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| CASNo = 688-73-3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| SMILES = CCCC(CCCC)CCCC |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 4XDX163P3D |
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| Section2 = {{Chembox Properties |
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| PubChem = 5948 |
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| Formula = C<sub>12</sub>H<sub>28</sub>Sn |
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| ChemSpiderID = 5734 |
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| MolarMass = 291.06 g/mol |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| Density = 1.082 g/mL |
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| EINECS = 211-704-4 |
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| MeltingPt = |
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| MeSHName = Tributyltin |
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| BoilingPt = 80 °C at 0.4 mm Hg |
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| ChEBI = 27086 |
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| Beilstein = 3587329 |
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| Gmelin = 4258 |
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| SMILES = CCCC(CCCC)CCCC |
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| StdInChI = 1S/3C4H9.Sn.H/c3*1-3-4-2;;/h3*1,3-4H2,2H3;; |
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| StdInChIKey = DBGVGMSCBYYSLD-UHFFFAOYSA-N |
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|Section2={{Chembox Properties |
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| Formula = {{Chem|SnC|12|H|28}} |
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| MolarMass = 291.06 g mol<sup>−1</sup> |
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| Density = 1.082 g cm<sup>−3</sup> |
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| BoilingPtC = 80 |
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| BoilingPt_notes = at 50 Pa |
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| Solubility = Slowly reacts{{Citation needed|date=September 2012}} |
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'''Tributyltin hydride''' is an ] with the formula (C<sub>4</sub>H<sub>9</sub>)<sub>3</sub>SnH. It is a colorless liquid that is soluble in organic solvents. The compound is used as a source of hydrogen atoms in ]. |
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'''Tributyltin hydride''' (Bu<sub>3</sub>SnH) is an ] compound. It is a useful reagent in ]. Combined with ] or by irradiation with light, tributyltin hydride cleaves to form the tributyltin ] (Bu<sub>3</sub>Sn'), which reacts with (an organic) substrate by substitution of a ] atom for a hydrogen atom in a ].<ref name="Clayden">, J. Clayden, N. Greeves, S. Warren and P. Wothers, in ''Organic Chemistry'', 2000, OUP, Oxford, ch. 39, pp. 1040-1041.</ref> |
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==Synthesis and characterization== |
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The compound is produced by reduction of ] 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> |
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: 2 "<sub>n</sub>" + (Bu<sub>3</sub>Sn)<sub>2</sub>O → "<sub>n</sub>" + 2 Bu<sub>3</sub>SnH |
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It can also be synthesized by a reduction of ] with ]. |
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The hydride is a distillable liquid that is mildly sensitive to air, decomposing to (Bu<sub>3</sub>Sn)<sub>2</sub>O. Its ] exhibits a strong band at 1814 cm<sup>−1</sup> for ''ν''<sub>Sn−H</sub>. |
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==Applications== |
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{{See also|Barton–McCombie deoxygenation}} |
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It is a specialized reagent in ]. Combined with ] (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 Bu<sub>3</sub>Sn<sup>•</sup>.<ref name="Clayden">, 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 |
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2004, John Wiley & Sons. {{doi|10.1002/047084289X.rt181.pub2}}</ref> The radical abstracts a H<sup>•</sup> from another equivalent of tributyltin hydride, propagating the chain. Tributyltin hydride's utility as a H<sup>•</sup> 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> |
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It is the reagent of choice for ] 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> |
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:RC<sub>2</sub>R′ + HSnBu<sub>3</sub> → RC(H)=C(SnBu<sub>3</sub>)R′ |
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==See also== |
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==See also== |
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* ] |
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* ] |
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== References == |
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{{reflist}} |
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{{Reflist}} |
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==Further reading== |
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* 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}} |
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