Tributyltin hydride is an
organotin compound
Organotin compounds or stannanes are chemical compounds based on tin with hydrocarbon substituents. Organotin chemistry is part of the wider field of organometallic chemistry. The first organotin compound was diethyltin diiodide (), discovered ...
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
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 (20 ...
with polymethylhydrosiloxane:
: 2 "
eSi(H)Osub>n" + (Bu
3Sn)
2O → "
eSi(OH)O
ESI or Esi may refer to:
Science and technology
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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 functio ...
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
Azobisisobutyronitrile (abbreviated AIBN) is an organic compound with the formula CH3)2C(CN)sub>2N2. 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 r ...
(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 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 importanc ...
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 bott ...
*
Trimethylsilyl
A trimethylsilyl group (abbreviated TMS) is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom minus;Si(CH3)3 which is in turn bonded to the rest of a molecule. This structural group is ch ...
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