Abstract
The reaction of ambident allylic halides with magnesium reagents was found to proceed by two alternative processes, i. e., nucleophilic substitution vs. single electron transfer, the contribution of each path being a marked function of various factors including steric and electronic effects of the substituent, solvents, and additives. Moreover, a remarkable difference in proportion of the two alkylation products was observed between these mechanistic alternatives. In the reaction of allylic lithiums with alkyl halides also the same trends were observed.
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