Electron-transfer substitution reactions: The p-nitrocumyl system

Article abstract of DOI:10.1021/jo00378a008

Facile substitution reactions at the tertiary carbon of p-nitrocumyl chloride and α,p-dinitrocumene are described. These reactions occur with a wide range of organic and inorganic nucleophiles and are noteworthy for providing novel and powerful means of synthesis; they occur readily under mild conditions, give excellent yields of pure products, and, in contrast to S_N2 displacements, are rather insensitive to steric hindrance. They are, therefore, especially valuable for the preparation of highly branched compounds. The view that these are electron-transfer chain processes derives from inhibition studies and, also, from the fact that these reactions are induced by one-electron-transfer agents.