Journal
ORGANIC LETTERS
Volume 9, Issue 4, Pages 611-613Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0628661
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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.
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