Hypervalent iodine reagents in organic synthesis: Nucleophilic substitution of p-substituted phenol ethers

The novel hypervalent iodine-induced nucleophilic substitution of p-substituted phenol ethers in the presence of a variety of nucleophiles and the direct alkyl azidation of p-alkyl phenol ethers are described UV and ESR spectroscopic studies indicate that these reactions proceed via radical species; one is [ArH+.] and the other is [ArC(.)R(1)R(2)] as reactive intermediates.