Abstract
The dye-sensitized photooxygenation of a series of methoxybenzenes (Ia-Ie) in methanol has been investigated. Highly substituted methoxybenzenes (Ig, Ii-Il) were susceptible to photooxygenation, while less substituted methoxybenzenes (Ia-Ig, Ih) were found to be unreactive under similar conditions. The participation of singlet oxygen in the reaction was elucidated by photooxygenation using sensitizers having different triplet energies and by quenching experiments. Relative reaction rates of methoxybenzenes with singlet oxygen were shown to correlate with their half-wave oxidation potentials (E 1 2 ) and with their charge-transfer maxima ( v c.t. ) with tetracyanoethylene.
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