Organotin oxides

When an organotin oxide or alkoxide is the starting material, reduction is performed with LiAlFLt221 or organosilicon hydrides like methylhydropolysiloxane (MeHSiO) 222,... 

Hydrolysis of the tin halides gives a family of important organotin oxides and hydroxides that have attracted a lot of attention in recent years. These compounds are considered in Section 3.14.16. 

A closely related method, which often gives higher yields, involves treatment of the hydroxy acids with 1-methyl- or l-phenyl-2-halopyridinium salts, especially l-methyl-2-chloropyri-dinium iodide (Mukaiyama s reagent).6 3 Another method uses organotin oxides.644... 

Alkyl halides can be converted to symmetrical ethers by treatment with oxide ion generated in situ by a reaction between an organotin oxide and fluoride ion in the presence of a quaternary ammonium iodide or a crown ether.715... 

Organotin oxides, R2SnO or (RjSnLO, prepared by treatment of the organotin halides with alkali. 

The alkyltin hydrides react slowly with water to form oxides or hydroxides. The reaction is more rapid with aqueous alkali, and hydrogen is evolved in addition to the formation of the organotin oxide or hydroxide. 

A. G. Davies Synthesis 56 (1969) The potential of organotin oxides and alkoxides 9... 

When the initial insertion involves an organotin oxide rather than an alkoxide, the reaction of a second isocyanate molecule induces decarboxylation to give a distannylurea by a process given earlier [reaction (j), 11.5.1], and then a third molecule inserts to give a distannylbiuret ... 

Finally, if the addendum is the organotin oxide, the first acceptor is an isocyanate and the second acceptor is an isothiocyanate, the decarboxylation stage is followed by elimination of bis(tributyltin) sulfide, providing a route to carbodiimides ... 

Analogous carbonyl-forming eliminations occur with the adducts formed between organotin oxides or alkoxides and trihalogenomethyl aldehydes or ketones, and tributyl-trichloromethyltin was first prepared by the elimination of methyl trichloroacetate from the adduct of tributyltin methoxide and hexachloroacetone.135 136... 

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