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Tributyltin hydride

Tributyltin hydride is an organotin compound 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 organic synthesis.

Synthesis and characterization

The compound is produced by reduction of tributyltin oxide with polymethylhydrosiloxane:

2 "[MeSi(H)O]<sub>n</sub>" + (Bu<sub>3</sub>Sn)<sub>2</sub>O → "[MeSi(OH)O]<sub>n</sub>" + 2 Bu<sub>3</sub>SnH

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 (Bu<sub>3</sub>Sn)<sub>2</sub>O. Its IR spectrum exhibits a strong band at 1814&nbsp;cm<sup>−1</sup> for ν<sub>Sn−H</sub>.

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 Bu<sub>3</sub>Sn<sup>•</sup>. 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).

It is the reagent of choice for hydrostannylation reactions:

RC<sub>2</sub>R′ + HSnBu<sub>3</sub> → RC(H)=C(SnBu<sub>3</sub>)R′

See also

References

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.