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Allyl bromide and tin reacted in aqueous media to give first allyltin(II) bromide ( 5 ) and then diallyltin dibromide ( 4 ). Either organotin intermediate can react with carbonyl compounds to give the corresponding homoallylic alcohols. Competitive experiment showed that 5 was more reactive than 4 .
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Chan et al. (1999) studied this question.
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