A. Griesbeck, Mi-Za Cho
Jan 27, 2007
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0
Influential Citations
57
Citations
Journal
Organic letters
Abstract
The visible-light irradiation of 9-mesityl-10-methylacridinium perchlorate 1 in the presence of monoalkenes and molecular oxygen leads to typical products of singlet oxygen addition (type II photooxygenation). The molecular probes 1-methylcyclohexene and limonene, respectively, result in hydroperoxide mixtures with a characteristic product pattern. A switch in the oxidative mechanism (electron-transfer photooxygenation) is observed for naphthalene derivatives as electron-rich acceptor molecules, revealing that the 9-mesityl-10-methylacridinium cation serves as a dual sensitizer with the capacity of efficient singlet oxygen formation and electron-transfer reaction. [reaction: see text].