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Triphenyltin hydride

Triphenyltin hydride is the organotin compound with the formula (C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>SnH, often abbreviated as , where Ph stands for phenyl. It is a colorless distillable oil that is soluble in organic solvents. It is often used as a source of "H·" to generate radicals or cleave carbon-oxygen bonds.

Preparation and reactions

Ph<sub>3</sub>SnH, as it is more commonly abbreviated, is prepared by treatment of triphenyltin chloride with lithium aluminium hydride. Although Ph<sub>3</sub>SnH is treated as a source of "H·", in fact it does not release free hydrogen atoms, which are extremely reactive species. Instead, Ph<sub>3</sub>SnH transfers H to substrates usually via a radical chain mechanism. This reactivity exploits the relatively good stability of "Ph<sub>3</sub>Sn·"

References