The effects of intramolecular hydrogen bonding on the electron-transfer properties of a series of bisphenol derivatives as compared with those of monophenol derivatives in which a hydroxy group is replaced by a methoxy group have been investigated in relation with their photographic properties. The oxidation of bisphenol derivatives with one-electron oxidants occurs to give the radical cation, followed by the deprotonation to produce the phenoxyl radical. Both the radical cations and phenoxyl radicals have been detected by laser flash photolysis measurements. Rates of hydrogen-transfer reactions from a series of bisphenol derivatives to cumylperoxyl radicals have been determined by monitoring the decay of the ESR signal due to cumylperoxyl radical produced by photoirradiation of an oxygen-saturated propionitrile solution of cumene and di- t -butylperoxide in the presence of bisphenol derivatives. The intramolecular hydrogen bonding plays an important role in determining the overall oxidation reactivity in the two-electron oxidation process by decreasing the one-electron oxidation potentials and also by facilitating the deprotonation step from the bisphenol radical cation to produce a phenoxyl radical.