Tributyltin hydride
Today, Tributyltin hydride is a topic that arouses great interest and debate in various areas of society. Its relevance and impact have generated conflicting opinions and have led to multiple studies and investigations that seek to delve deeper into its implications. Without a doubt, Tributyltin hydride is a question that is constantly evolving, adapting to the changes and challenges of today's world. Through this article, we will explore different perspectives and approaches on Tributyltin hydride, with the aim of analyzing its importance and understanding its influence on our daily lives.
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| Names | |||
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| Systematic IUPAC name
Tributylstannane[1] | |||
| Identifiers | |||
3D model (JSmol)
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| 3587329 | |||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.010.642 | ||
| EC Number |
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| 4258 | |||
| MeSH | Tributyltin | ||
PubChem CID
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| UNII | |||
CompTox Dashboard (EPA)
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| Properties | |||
| SnC 12H 28 | |||
| Molar mass | 291.06 g mol−1 | ||
| Density | 1.082 g cm−3 | ||
| Boiling point | 80 °C (176 °F; 353 K) at 50 Pa | ||
| Slowly reacts[citation needed] | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
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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 "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−1 for νSn−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•.[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
- ^ "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