Kalpana Kalpana (Editor)

Tributyltin hydride

Updated on
Edit
Like
Comment
Share on FacebookTweet on TwitterShare on LinkedInShare on Reddit
Formula
  
SnC12H28

Density
  
1.08 g/cm³

Gmelin Reference
  
4258

Molar mass
  
291.06 g/mol

Beilstein Reference
  
3587329

Pubchem
  
5948

Tributyltin hydride httpsuploadwikimediaorgwikipediacommonsthu

Boiling point
  
80 °C (176 °F; 353 K) at 50 Pa

A16 reductive dehalogenation with tributyltin hydride reaction mechanism


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.

Contents

Synthesis and characterization

The compound is produced by reduction of tributyltin oxide with polymethylhydrosiloxane (Bu = CH3CH2CH2CH2):

2"(MeSiH)" + (Bu3Sn)2O → "(Me2Si)2O" + 2 Bu3SnH(Bu3Sn)2O + 2/n (MeSi(H)O)n → 2 Bu3SnH + 1/n [(MeSiO)2O]n

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 useful 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•. 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). Recently, transition metal hydrides have emerged as attractive alternatives to tin hydrides, as transition metal hydrides can be used catalytically and have more variety in bond strength.

References

Tributyltin hydride Wikipedia


Similar Topics