Tributyltin hydride
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| Template:Longitem | 3587329 |
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| Template:Longitem | 4258 |
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| MeSH | Tributyltin |
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| Molar mass | 291.06 g mol−1 |
| Density | 1.082 g cm−3 |
| Boiling point | Template:Chembox CalcTemperatures |
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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:[2][3]
- 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 νSn−H.
Applications
Script error: No such module "Labelled list hatnote". 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•.[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]
It is the reagent of choice for hydrostannylation reactions:[7]
- RC2R′ + HSnBu3 → RC(H)=C(SnBu3)R′
See also
References
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- ↑ Script error: No such module "citation/CS1".
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- ↑ 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. Script error: No such module "CS1 identifiers".
- ↑ 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 Script error: No such module "CS1 identifiers".
- ↑ Script error: No such module "Citation/CS1".
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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. Script error: No such module "CS1 identifiers".