Organotin Alkoxides, Phenoxides, and Peroxides

Organotin alkoxides and phenoxides can be prepared from the reaction of an alkali metal alkoxide or phenoxide with the appropriate organotin halide. Triorganotin alkoxides and phenoxides are available from the reaction of bis(triorganotin) oxides with alcohols or phenols or the corresponding carbonates, and the amides R Sn(NR 2)4 react with alcohols to give the corresponding alkoxides. 

Alkoxystannanes can also be prepared by the addition of an organotin hydride to a carbonyl compound (equation 14-5), and by the Sh2 reaction of alkoxyl radicals with organotin compounds carrying electronegative ligands (Section 11.4), for example equation 14-6, but these reactions have not been widely used for preparative purposes. 

Reaction 14-1 can be used for making mono-, di-, or tri-alkoxides (n = 3, 2 or 1) (equations 14-7-14-9) though the reaction between organotin trihalides and sodium alkoxides is complete only when the reagents are heated together in benzene under reflux for some hours.2,3 

Organotin Chemistry, Second Edition. Alwyn G. Davies Copyright 2004 Wiley-VCH Verlag GmbH Co. KGaA. ISBN 3-527-31023-1 

The sodium halide which is formed in these reactions is very finely divided, and may be difficult to filter off.2 A more convenient way of preparing the triorganotin alkoxides and phenoxides is by the azeotropic dehydration of a mixture of the bis(trialkyltin) oxide and alcohol or phenol in a solvent such as benzene or toluene.4 

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