Oxygenation of α-methylstyrene with molecular oxygen, catalyzed by 10-methylacridinium ion via photoinduced electron transfer

Kyou Suga, Kei Ohkubo, Shunichi Fukuzumi

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57 Scopus citations

Abstract

Photooxygenation of α-methylstyrene with oxygen occurs efficiently in the presence of 10-methylacridinium perchlorate (AcrH+ClO4-) under visible light irradiation in oxygen-saturated acetonitrile (MeCN) to yield acetophenone as the main oxygenated product. No photoinduced oxygenation of α-methylstyrene occurs in the absence of AcrH+ under otherwise the same experimental conditions. Little photodegradation of AcrH- occurs in the present photocatalytic system, which provides a clean method of photoinduced oxygenation reaction with molecular oxygen, alternate to the ene reaction of singlet oxygen. The photocatalytic oxygenation of α-methylstyrene with oxygen is shown to proceed via photoinduced electron transfer from α-methylstyrene to the singlet excited state of AcrH- (1AcrH+*) on the basis of the fluorescence quenching of 1AcrH+* by α-methylstyrene, the quantum yield determination, and the detection of radical intermediates by laser flash photolysis and ESR measurements.

Original languageEnglish
Pages (from-to)4339-4346
Number of pages8
JournalJournal of Physical Chemistry A
Volume107
Issue number22
DOIs
StatePublished - 5 Jun 2003

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