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| ImageFileL1 = Tributyltin hydride.svg | | ImageFileL1 = Tributyltin hydride.svg | ||
| ImageFileL1_Ref = {{chemboximage|correct|??}} | | ImageFileL1_Ref = {{chemboximage|correct|??}} | ||
| ImageSizeL1 = 121 | |||
| ImageNameL1 = Skeletal formula of tributyltin with one explicit hydrogen added | | ImageNameL1 = Skeletal formula of tributyltin with one explicit hydrogen added | ||
| ImageFileR1 = Tributyltin.png | | ImageFileR1 = Tributyltin hydride.png | ||
| ImageFileR1_Ref = {{chemboximage|correct|??}} | | ImageFileR1_Ref = {{chemboximage|correct|??}} | ||
| ImageSizeR1 = 121 | |||
| ImageNameR1 = Spacefill model of tributyltin | | ImageNameR1 = Spacefill model of tributyltin | ||
| ImageFile2 = Tributyltin-hydride-3D-balls.png | | ImageFile2 = Tributyltin-hydride-3D-balls.png | ||
| ImageFile2_Ref = {{chemboximage|correct|??}} | | ImageFile2_Ref = {{chemboximage|correct|??}} | ||
| ImageSize2 = 244 | |||
| ImageName2 = Ball and stick model of tributyltin | | ImageName2 = Ball and stick model of tributyltin | ||
| SystematicName = Tributylstannane<ref>{{Cite web|url = |
| 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 | ||
| |
| CASNo_Ref = {{cascite|correct|CAS}} | ||
| UNII_Ref = {{fdacite|correct|FDA}} | |||
| PubChem = 5948 | |||
| UNII = 4XDX163P3D | |||
| PubChem_Ref = {{Pubchemcite|correct|pubchem}} | |||
| |
| PubChem = 5948 | ||
| ChemSpiderID = 5734 | |||
| |
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ||
| |
| EINECS = 211-704-4 | ||
| MeSHName = Tributyltin | |||
| ChEBI_Ref = {{ebicite|changed|EBI}} | | MeSHName = Tributyltin | ||
| ChEBI_Ref = {{ebicite|changed|EBI}} | |||
| ChEBI = 27086 | | ChEBI = 27086 | ||
| |
| Beilstein = 3587329 | ||
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| Gmelin = 4258 | ||
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| SMILES = CCCC(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 | ||
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| Formula = {{Chem|SnC|12|H|28}} | ||
| |
| MolarMass = 291.06 g mol<sup>−1</sup> | ||
| |
| Density = 1.082 g cm<sup>−3</sup> | ||
⚫ | | BoilingPtC = 80 | ||
| Density = 1.082 g cm<sup>-3</sup> | |||
| BoilingPt_notes = at 50 Pa | |||
⚫ | | |
||
⚫ | | Solubility = Slowly reacts{{Citation needed|date=September 2012}} | ||
| Boiling_notes = at 50 Pa | |||
⚫ | | |
||
}} | }} | ||
}} | }} | ||
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==Synthesis and characterization== | ==Synthesis and characterization== | ||
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> | |||
⚫ | |||
⚫ | : 2 "<sub>n</sub>" + (Bu<sub>3</sub>Sn)<sub>2</sub>O → "<sub>n</sub>" + 2 Bu<sub>3</sub>SnH | ||
{{OrgSynth | |||
It can also be synthesized by a reduction of ] with ]. | |||
|author=Jordi Tormo and Gregory C. Fu | |||
|year=2002 | |||
|title=Tributylstannane (Bu<sub>3</sub>SnH)-Catalyzed ] of Alcohols: 3-Deoxy-1,2:5,6-bis-O-(1-methylethyilidine)-α-D-ribo-hexafuranose | |||
|volume=78 | |||
|pages=239 | |||
|collvol= | |||
|collvolpages= | |||
|prep=}}</ref> | |||
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>. | |||
⚫ | :(Bu<sub>3</sub>Sn)<sub>2</sub>O |
||
The hydride is a distillable liquid that is mildly sensitive to air, decomposing to (Bu<sub>3</sub>Sn)<sub>2</sub>O. Its IR spectrum exhibits a strong band at 1814 cm<sup>-1</sup> for ν<sub>Sn-H</sub>. | |||
==Applications== | ==Applications== | ||
{{See also|Barton–McCombie deoxygenation}} | |||
It is a |
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 | ||
2004, John Wiley & Sons. {{DOI|10.1002/047084289X.rt181.pub2}}</ref> | |||
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> | |||
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> | |||
:RC<sub>2</sub>R′ + HSnBu<sub>3</sub> → RC(H)=C(SnBu<sub>3</sub>)R′ | |||
==See also== | ==See also== | ||
* ] | * ] | ||
* ] | |||
== References == | == References == | ||
{{Reflist}} | {{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}} | ||
] | ] | ||
] | ] | ||
] | |||
] | |||
] |
Latest revision as of 22:34, 23 August 2024
| |||
Names | |||
---|---|---|---|
Systematic IUPAC name Tributylstannane | |||
Identifiers | |||
CAS Number | |||
3D model (JSmol) | |||
Beilstein Reference | 3587329 | ||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.010.642 | ||
EC Number |
| ||
Gmelin Reference | 4258 | ||
MeSH | Tributyltin | ||
PubChem CID | |||
UNII | |||
CompTox Dashboard (EPA) | |||
InChI
| |||
SMILES
| |||
Properties | |||
Chemical formula | SnC 12H 28 | ||
Molar mass | 291.06 g mol | ||
Density | 1.082 g cm | ||
Boiling point | 80 °C (176 °F; 353 K) at 50 Pa | ||
Solubility in water | Slowly reacts | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references |
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:
- 2 "n" + (Bu3Sn)2O → "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 for νSn−H.
Applications
See also: Barton–McCombie deoxygenationIt 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. 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).
It is the reagent of choice for hydrostannylation reactions:
- RC2R′ + HSnBu3 → RC(H)=C(SnBu3)R′
See also
References
- "SnBu3H - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
- Maleczka, Robert E.; Terrell, Lamont R.; Clark, Damon H.; Whitehead, Susan L.; Gallagher, William P.; Terstiege, Ina (1999). "Application of Fluoride-Catalyzed Silane Reductions of Tin Halides to the in Situ Preparation of Vinylstannanes". J. Org. Chem. 64 (16): 5958–5965. doi:10.1021/jo990491+.
- Tormo, J.; Fu, G. C. (2002). "α-D-Ribo-hexofuranose, 3-deoxy-1,2:5,6-bis-O-(1-methylethylidene)". Org. Synth. 78: 239. doi:10.15227/orgsyn.078.0239.
- 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
- 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
- Smith, Nicholas D.; Mancuso, John; Lautens, Mark (2000). "Metal-Catalyzed Hydrostannations". Chemical Reviews. 100 (8): 3257–3282. doi:10.1021/cr9902695. PMID 11749320.
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