| 词条 | Tributyltin hydride |
| 释义 |
| 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[1] |Section1={{Chembox Identifiers | CASNo = 688-73-3 | CASNo_Ref = {{cascite|correct|CAS}} | 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 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 characterizationThe compound is produced by reduction of tributyltin oxide with polymethylhydrosiloxane (Bu = CH3CH2CH2CH2):[2][3] 2"(MeSiH)" + (Bu3Sn)2O → "(Me2Si)2O" + 2 Bu3SnH (Bu3Sn)2O + 2/n (MeSi(H)O)n → 2 Bu3SnH + 1/n [(MeSiO)2O]n 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 νSn-H. ApplicationsIt is a useful 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•.[4][5] 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).[6] Recently, transition metal hydrides have emerged as attractive alternatives to tin hydrides, as transition metal hydrides can be used catalytically and have more variety in bond strength. See also
References1. ^{{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}} 2. ^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}} 3. ^{{OrgSynth| author=Jordi Tormo and Gregory C. Fu| year=2002| title=Tributylstannane (Bu3SnH)-Catalyzed Barton-McCombie deoxygenation of Alcohols: 3-Deoxy-1,2:5,6-bis-O-(1-methylethyilidine)-α-D-ribo-hexafuranose| volume=78| pages=239| collvol=| collvolpages=| prep=}} 4. ^OUP catalogue page, J. Clayden, N. Greeves, S. Warren and P. Wothers, in Organic Chemistry, 2000, OUP, Oxford, ch. 39, pp. 1040-1041. 5. ^T. V. (Babu) RajanBabu, Philip C. Bulman Page, Benjamin R. Buckley, "Tri-n-butylstannane" Encyclopedia of Reagents for Organic Synthesis2004, John Wiley & Sons. {{DOI|10.1002/047084289X.rt181.pub2}} 6. ^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}} 3 : Organotin compounds|Radical initiators|Metal hydrides |
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