Electron Transfer Rate Determinations: Facile Electron Transfer from 1,1,2,2-Tetrakis(4-methoxyphenyl)ethanediol

Article abstract of DOI:10.1021/jo00060a009

The oxidation reactions of 1,1,2,2-tetrakis(4-methoxyphenyl)ethanediol, 1, by 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) and Fe(III) complexes have been found to proceed cleanly in the presence of an appropriate base to give 4,4'-dimethoxybenzophenone.The rates of oxidation of 1,1,2,2-tetrakis(4-methoxyphenyl)ethanediol by 2,3-dichloro-5,6-dicyanobenzoquinone and Fe(III)(4-methoxy-2,2'-bipyridyl)3(ClO4)3 have been measured.Evaluation of the rate constants has allowed calculation of E₀(excit.) for 1.Compared to 4-methoxytoluene, 1 is much easier to oxidize, following the general trend that phenyl-phenyl interactions lower the oxidation potentials of tetraarylethanediols relative to their corresponding monoaryl model compounds.