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 (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 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 with polymethylhydrosiloxane:
: 2 "
eSi(H)Osub>n" + (Bu
3Sn)
2O → "
eSi(OH)Osub>n" + 2 Bu
3SnH
It can also be synthesized by a reduction of
tributyltin chloride 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 (Bu
3Sn)
2O. Its
IR spectrum 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 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 ...
. 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
*
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 i ...
References
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. {{doi, 10.1016/S0022-328X(00)81719-2
Organotin compounds
Radical initiators
Metal hydrides
Tin(IV) compounds
Butyl compounds