Steady-state and nanosecond spectroscopic studies of triplet sensitized reaction of K-region arene oxides |
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Authors: | Michiya Itoh Kenji Murata Kunihiro Tokumura Koichi Shudo Naoki Miyata Toshihiko Okamoto |
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Affiliation: | Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi, Kanazawa 920, Japan;Faculty of Pharmaceutical Sciences, The University of Tokyo, Bunkyo-ku Tokyo 113, Japan |
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Abstract: | Photorearrangement reactions of K-region arene oxides, 9,10-epoxy-9,10-dihydrophenanthrene (1a), 3-acetyl-9,10-epoxy-9,10-dihydrophenanthrene (1b), and 3,4-epoxy-3,4-dihydropyrene (1c) in dichloroethane (DCE) solution were investigated by steady irradiation and nanosecond transient spectroscopy. Photorearrangements producing substituted oxepins, 2 occur via the singlet excited state of these compounds, while the phenolic products, 9-hydroxyphenanthrene (3a), 3-acetyl-9-hydroxyphenanthrene (3b), and 4-hydroxypyrene (3c) are formed via the triplet state. Phenol 3 formation from the triplet 1 sensitized by the triplet 3 (i.e. product sensitization) is proposed for the photorearrangement reactions of 1a and 1c, and this process is the only way phenol (3a) is formed because of the negligible intersystem crossing probability of 1a. No product sensitization occurs in the photorearrangement reaction of 1b. |
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