Phenoxy radicals, from decomposition

Phenolic compounds may enhance the rate of decomposition of aromatic ether, because the phenoxy radical may be stabilized by solvation (18) or hydrogen bonding (19) with phenolic compounds and may result in the subsequent hydrogen transfer reaction from hydrogen donating solvent or phenols (20). 

However, detailed analysis for this oxidation reaction showed that the reaction mechanism did not involve radical intermediates hut rather a henzoyl perester intermediate (15). It was reported that the thermal decomposition of henzoyl 2,6-dimethylphenyl carbonate, which should generate the phenoxy radical, produced Poly-2,6-Me2P and DPQ in 35-38% and 10% yield, respectively (16). From these studies, it seems that some complicated experimental results and different imder-standings were involved in the above assumption of the C—C coupling selectivity in the free-radical coupling, which was pointed out before (17). 

---