Abstract
Reaction of 2,6-di-t-butylphenol (I) with chemically generated singlet oxygen gives 2,6-di-t-butylbenzoquinone (II) and 3,5,3′,5′-tetra-t-butyldiphenoquinone (III), indicating that singlet oxygen participates in the hydrogen abstraction from I to form a phenoxy radical (IV). In order to see whether singlet oxygen plays a role in the rose bengal-sensitized photooxygenation of I, a competition reaction between I and a singlet oxygen acceptor (linalool), quenching by a singlet oxygen quencher (β-carotene), and the effect of concentrations of I were examined. The results show that both of singlet oxygen and the triplet excited sensitizer are responsible for the hydrogen abstraction from I in the photosensitized oxygenation.
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