Tributyltin hydride is an

organotin compound Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide (), discovered ...

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 Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

Synthesis and characterization

The compound is produced by reduction of

tributyltin oxide Tributyltin oxide (TBTO) is an organotin compound chiefly used as a biocide (fungicide and molluscicide), especially a wood preservative. Its chemical formula is C4H9)3Snsub>2O. It is a colorless viscous liquid. It is poorly soluble in water (2 ...

with polymethylhydrosiloxane: : 2 "

eSi(H)O ESI or Esi may refer to: Science and technology * Earth Similarity Index * Electrospray ionization, a technique used in mass spectrometry * Environmental Seismic Intensity scale * Essential Science Indicators, by Clarivate * Electronic supplement ...

sub>n" + (Bu₃Sn)₂O → "

eSi(OH)O ESI or Esi may refer to: Science and technology * Earth Similarity Index * Electrospray ionization, a technique used in mass spectrometry * Environmental Seismic Intensity scale * Essential Science Indicators, by Clarivate * Electronic supplement ...

sub>n" + 2 Bu₃SnH It can also be synthesized by a reduction of

tributyltin chloride Tributyltin chloride is an organotin compound with the formula ( C4H9)3SnCl. It is a colorless liquid that is soluble in organic solvents. Preparation and reactions The compound is prepared by a redistribution reaction by combining stannic chlo ...

with

lithium aluminium hydride Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula or . It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthe ...

. 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 ''ν''_Sn−H.

Applications

It is a specialized reagent in

. Combined with

azobisisobutyronitrile Azobisisobutyronitrile (abbreviated AIBN) is an organic compound with the formula . This white powder is soluble in alcohols and common organic solvents but is insoluble in water. It is often used as a foamer in plastics and rubber and as a radic ...

(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^•.OUP catalogue page
J. Clayden, N. Greeves, S. Warren and P. Wothers, in ''Organic Chemistry'', 2000, OUP, Oxford, ch. 39, pp. 1040-1041. 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 In chemistry, hydrostannylation is the insertion of unsaturated substrates into an Sn-H bond. The reaction occurs under free-radical conditions, but the stereochemistry and regiochemistry are often complex. The reaction gained synthetic importance ...

reactions: :RC₂R′ + HSnBu₃ → RC(H)=C(SnBu₃)R′

Synthesis and characterization

Applications

See also

References

Further reading