Electron Apportionment in Cleavage of Radical Anions. 2. Naphthylmethyl Phenyl Ethers vs. Naphthyl Benzyl Ethers

Article abstract of DOI:10.1021/ja00270a022

Naphthylmethyl phenyl ethers and naphthyl benzyl ethers were found to undergo scission of the H2C-O bond when treated with radical anions of anthracene or fluoranthene.Under comparable conditions, ethers of the naphthylmethyl phenyl series (α and β) reacted more than 10E4 times faster than ethers of the naphthyl benzyl series (α and β).This preference for regioconservation of spin density in the scission process is interpreted in terms of ?-bond polarization at the transition state.