Triphenyltin hydride is the

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 by ...

with the formula (C₆H₅)₃SnH. It is a white distillable oil that is soluble in organic solvents. It is often used as a source of "H·" to generate

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or cleave carbon-oxygen bonds.

Preparation and reactions

Ph₃SnH, as it is more commonly abbreviated, is prepared by treatment of triphenyltin chloride with

lithium aluminium hydride Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li Al H4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic ...

.Clive, D. L. J. "Triphenylstannane" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. Although Ph₃SnH is treated as a source of "H·", in fact it does not release free

hydrogen atom A hydrogen atom is an atom of the chemical element hydrogen. The electrically neutral atom contains a single positively charged proton and a single negatively charged electron bound to the nucleus by the Coulomb force. Atomic hydrogen consti ...

s, which are extremely reactive species. Instead, Ph₃SnH transfers H to substrates usually via a radical chain mechanism. This reactivity exploits the relatively good stability of "Ph₃Sn·"

References

{{reflist Metal hydrides Triphenyltin compounds Reagents for organic chemistry