Electron Apportionment in Cleavage of Radical Anions. 1. Nitro-Substituted Benzyl Phenyl Ethers

Article abstract of DOI:10.1021/ja00270a021

The radical anions of 4-nitrobenzyl phenyl ethers undergo cleavage at least 10E4 times faster than the radical anions of corresponding 4-nitrophenyl benzyl ethers despite a perceived thermodynamic advantage for the latter set of reactions.It is suggested that this results reflects a kinetic advantage for cleavage reactions which take place with regioconservation of spin density.