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Triphenyltin hydride is used as a source of "H·" to generate radicals or cleave carbon-oxygen bonds. And it is also used in anti-fouling paints.
Christopher J. Easton. Free-Radical Reactions in the Synthesis of α-Amino Acids and Derivatives. Chem. Rev. 1997, 97, (1), 53-82.
Andrew Evans, P.; Jamie D. Roseman. Stereoselective synthesis of cis-2,5-disubstituted tetrahydrofuran-3-ones via an acyl radical cyclization. Tetrahedron Letters. 1995, 36, (1), 31-34.
For general reactions of organotin hydrides, see Tri-n-butyltin hydride, A13298.
2-(Bromomethyl)penicillin V methyl ester undergoes ring-expansion via the methylene radical, to give the corresponding cepham: Tetrahedron, 44, 5953 (1988):
Hydrostannylation of terminal alkynes is conveniently carried out in the presence of triethylboron. Reaction is faster than with tributyl tin hydride and gives higher yields. Stereoselectivity varies from 69-100% (E): Tetrahedron, 45, 923 (1989):
Reagent for free-radical desulfurization of the thionocarbonates of 1,2-diols to the corresponding methylenedioxy compounds: J. Org. Chem., 62, 1690 (1997).
Gefahrenhinweise (EU): H301-H311-H331
Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled.
Avoid release to the environment. Wear protective gloves/clothing. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Dispose of contents/container in accordance with local/regional/national/international regulations.