Homolytic Allyl Transfer Reactions of 1- and 3-Alkyl-Substituted Allyltributylstannanes

Abstract

There have been several reports that homolytic allyl transfer reactions of 1- and 3-substituted allylstannanes are complicated by competing reactions.1-41,3-Rear-rangement of the allylstannane, under the normal reaction conditions for homolytic allyl group transfer, can affect the integrity of the stannane and of the allylation product.3 Alternatively, reduction of the substrate through hydrogen abstraction from the stannane can occur in preference to the allylation reaction.1,2 This is particularly the case in reactions of 3-alkyl-substituted allylstannanes, where the steric effect of the alkyl substituent slows the rate of addition of radicals to the stannane, thus facilitating the competing reduction process. Only Pereyre and co-work-ers5 have reported homolytic allyl transfer reactions of tributyl(3-methylallyl)stannane (5b). Show more