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Abstract
Di-n-butyltin oxide (DBTO), with the composition Bu2SnO, is an amorphous, polymeric powder insoluble in nonreacting solvents. It has been widely used for the selective manipulation of hydroxyl groups and polyols. The largest application of DBTO in organic chemistry is in the generation and reactions of stannylenes from polyhydroxy compounds. The stannylene acetals may be prepared by refluxing equimolar mixtures of substrate and DBTO in benzene or toluene, with a Dean-Stark apparatus. [1] Recently, Simas has reported that the stannylene intermediate formation does not require removal of water. [2] The synthesis of di-n-butylstannylene is faster in methanol, but this solvent must be removed prior to addition of the electrophile. [3] Formation of these tin derivatives can be greatly accelerated by microwave irradiation. [4]
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