Journal of Organic Chemistry p. 2003 - 2008 (1993)
Update date:2022-08-11
Topics:
Penn, John H.
Duncan, Joseph H.
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.
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