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Bis(tri-n-butyltin) oxide is employed in the synthesis of α,β-unsaturated methyl ketones, isoxazoles.
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 .
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 .
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).
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):
Converts thioamides to nitriles, as does Di-n-butyltin oxide, L14491: J .Org. Chem., 47, 4594 (1982).
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).
Hazard Statements: H301-H311-H315-H319-H360-H372
Toxic if swallowed. Toxic in contact with skin. Causes skin irritation. Causes serious eye irritation. May damage fertility or the unborn child. Causes damage to organs through prolonged or repeated exposure.
Precautionary Statements: P273-P280-P309-P310a-P501a
Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. IF exposed or if you feel unwell: Immediately call a POISON CENTER/doctor Dispose of contents/container in accordance with local/regional/national/international regulations.