Radiation studies of aryl glycosides : Part VI. Radicals derived from Phenyl β-d-glucopyranosides

Radicals formed by γ-irradiation of o-, m-, and p-substituted-phenyl β-d-glucopyranosides have been studied in the polycrystalline state, in glassy methanol, and in frozen, aqueous solution. Substituted cyclohexadienyl radicals and radicals derived from the d-glucopyranosyl group are evident after irradiation of the compounds in the solid state and in frozen, aqueous solutions. Cyclohexadienyl radicals are the more stable during thermal annealing and are present in 2–3 times greater yield than the sugar radicals. p-Hydroxy- and methoxy-phenyl β-d-glucopyranosides yield phenoxy radicals, which can be transformed into substituted cyclohexadienyl radicals by thermal annealing. Hydrogen abstraction and inter- and intra-molecular hydrogen-transfer are the most likely processes leading to the radicals which have been identified.