Photo-Fries rearrangement of 1-pyrenyl esters |
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| Authors: | Hajime Maeda Tomomi Akai Masahito Segi |
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| Affiliation: | Applied Chemistry Course, School of Chemistry, College of Science and Engineering, Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa 920-1192, Japan |
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| Abstract: | Photo-Fries rearrangement reactions of 1-pyrenyl esters were investigated. Photoreaction of 1-pyrenyl benzoate in benzene generates 1-hydroxy-2-pyrenyl phenyl ketone along with 1-pyrenol. The exceptionally down field 1H NMR chemical shift of OH proton in the photoproduct indicates the existence of intramolecular hydrogen bonding. Photorearrangements of analogs that have electron-withdrawing or electron-releasing group on the phenyl ring, and related heteroaromatic carboxylates also take place to form the corresponding ketones. However, photoreactions of 1-pyrenyl aliphatic carboxylate esters do not occur. The results of spectroscopic and theoretical studies suggest the mechanistic pathway for this process is initiated by homolytic C | |
| Keywords: | Photorearrangement Photo-Fries rearrangement Pyrene Pyrenyl ester Intramolecular hydrogen bonding |
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