Electron-transfer photooxygenation. 8. dicyanoanthracene-sensitized photooxidation of ortho-dimethoxybenzene |
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Authors: | Jang-Jeng Liang Christopher S. Foote |
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Affiliation: | Department of Chemistry, University of California, Los Angeles, California 90024 U.S.A. |
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Abstract: | Two cleavage products, -dimethylmuconate () and -dimethyl-muconate (), are inefficiently produced in the 9,10-dicyanoanthracene (DCA) sensitized photooxidation of -dimethoxybenzene (-DMB) in polar solvents. An electron transfer mechanism is proposed in which superoxide ion (O?20 combines with ortho-dimethoxybenzene to form a dioxetane (3), which cleaves to form (). The initial products is , which is rapidly converted to and other products under the conditions; cis-trans isomer is formed. |
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