Tributyltin hydride

Tributyltin hydride is an organotin compound with the formula 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:
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 ₂O. Its IR spectrum exhibits a strong band at 1814 cm⁻¹ for ν_Sn−H.

It is a specialized reagent in organic synthesis. Combined with azobisisobutyronitrile or by irradiation with light, tributyltin hydride converts organic halides 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.
It is the reagent of choice for hydrostannylation reactions: