Abstract
A new type of nucleophilic substitution reaction is described. These reactions proceed by a multistage pathway involving radical anions and free radicals as intermediates. They occur readily under mild conditions to give good yields of products, and in contrast to SN 2 displacement, they are insensitive to steric hindrance. Therefore, these reactions are valuable for the synthesis of highly branched structure. A number of examples of substitution at an aromatic carbon or at a vinylic carbon are also described. The synthesis of cephalotaxine has been achieved by intramolecular nucleophilic aromatic substitution of an enolate anion. A new olefin synthesis by one electron transfer processes is also described.
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