Triphenyltin hydride is the organotin compound 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 radicals

Radical (chemistry)

Radicals are atoms, molecules, or ions with unpaired electrons on an open shell configuration. Free radicals may have positive, negative, or zero charge...

 or cleave carbon-oxygen bonds.

Preparation and reactions

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

Triphenyltin chloride

Triphenyltin chloride is an organotin compound with formula Sn3Cl. It is a colourless solid that dissolves in organic solvents. It slowly reacts with water. The main for this compound is as fungicide and antifoulant.-Hazards:...

 with lithium aluminium hydride

Lithium aluminium hydride

Lithium aluminium hydride, commonly abbreviated to LAH or known as LithAl, is an inorganic compound with the chemical formula LiAlH4. It was discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters,...

. Although Ph₃SnH is treated as a source of "H·", in fact it does not release free hydrogen atom

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...

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·"