Tributyltin hydride is an
organotin compound with the formula (C
4H
9)
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 special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
.
Synthesis and characterization
The compound is produced by reduction of
tributyltin oxide with polymethylhydrosiloxane:
: 2 "
eSi(H)O
ESI or Esi may refer to:
Science and technology
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* Electrospray ionization
* Environmental Seismic Intensity scale
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* Electronic supplementary information, in scientific publica ...
sub>n" + (Bu
3Sn)
2O → "
eSi(OH)O
ESI or Esi may refer to:
Science and technology
* Earth Similarity Index
* Electrospray ionization
* Environmental Seismic Intensity scale
* Essential Science Indicators, by Clarivate
* Electronic supplementary information, in scientific publicat ...
sub>n" + 2 Bu
3SnH
The hydride is a distillable liquid that is mildly sensitive to air, decomposing to (Bu
3Sn)
2O. Its
IR spectrum
Infrared spectroscopy (IR spectroscopy or vibrational spectroscopy) is the measurement of the interaction of infrared radiation with matter by absorption, emission, or reflection. It is used to study and identify chemical substances or function ...
exhibits a strong band at 1814 cm
−1 for ''ν''
Sn−H.
Applications
It is a specialized reagent in
organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
. 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
3Sn
•.
[OUP catalogue page](_blank)
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 reactions:
:RC
2R′ + HSnBu
3 → RC(H)=C(SnBu
3)R′
See also
*
Tributyltin
Tributyltin (TBT) is an umbrella term for a class of organotin compounds which contain the (C4H9)3 Sn group, with a prominent example being tributyltin oxide. For 40 years TBT was used as a biocide in anti-fouling paint, commonly known as ...
*
Trimethylsilyl
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.
References
{{Reflist
Organotin compounds
Radical initiators
Metal hydrides
Tin(IV) compounds