Bis(tri-n-butyltin) oxide, 97%, Thermo Scientific Chemicals

General References:

1. E.I. Krajnc.; P.W. Wester.;J.G. Loeber.; F.X.R. van Leeuwen.; J.G. Vos.; H.A.M.G. Vaessen.; C.A. van der Heijden. Toxicity of bis(tri-n-butyltin)oxide in the rat: I. Short-term effects on general parameters and on the endocrine and lymphoid systems. Toxicol. Appl. Pharmacol. 1984, 75 (3),363-386 .
2. J.G. Vos.; A.De Klerk.; E.I. Krajnc.; H.Van Loveren.; J. Rozing. Immunotoxicity of Bis(tri-n-butyltin)oxide in the rat: Effects on thymus-dependent immunity and on nonspecific resistance following long-term exposure in young versus aged rats. Toxicol. Appl. Pharmacol. 1990, 105 (1),144-155 .
3. Reacts with alcohols to give tri-n-butylstannyl ethers which, for simple alcohols, are very susceptible to hydrolysis: Synthesis, 56 (1969); J. Organomet. Chem., 110, C57 (1976). In combination with bromine or NBS, allylic, benzylic and secondary alcohols are oxidized to carbonyl compounds, enabling the selective oxidation of secondary, in the presence of primary, alcohols: Bull. Chem. Soc. Jpn., 49, 1656 (1976); Tetrahedron Lett., 4597 (1976); J. Am. Chem. Soc., 98, 1629 (1976). Similarly, sulfides give sulfoxides with no over-oxidation to sulfones: Tetrahedron Lett., 2413 (1977).
4. Reacts with terminal alkynes to give alkynyl tin reagents. Where these reagents have electron-withdrawing substituents, they undergo regioselective cycloaddition with 1,3-dienes: Tetrahedron, 45, 1145 (1989):
5. Converts thioamides to nitriles, as does Di-n-butyl tin oxide, L14491: J .Org. Chem., 47, 4594 (1982).
6. Reagent for mild, selective non-hydrolytic deprotection of esters: Tetrahedron Lett., 32, 4239 (1991); J. Org. Chem., 59, 7259 (1994); Tetrahedron Lett., 36, 3311 (1995).