Abstracts of Symposium on Physical Organic Chemistry
53rd Symposium on Organic Reactions
Session ID : O-18
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Co-host: The Chemical Society of Japan, The Chemical Society of Japan, Kyushu Branch, The Society of Synthetic Organic Chemistry, Japan (Cooperation)

The First Oxa-analog of Tetramethyleneethane Radical Cation Generated in the Photoinduced Electron-Transfer Reactions of 2-Methylenecyclopropanes
*Hiroshi Ikeda, Futoshi Tanaka, Tsutomu Miyashi, Kimio Akiyama, Shozo Tero-Kubota
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Keywords: oxatetramethyleneethane, radical cation, methylenecyclobutanone, electron transfer, photoreaction
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Abstract
On irradiation of p-chloranil (CA), 2,2-bis(p-methoxyphenyl)-3,3-dimethyl-4-methylenecyclobutanone (1) gives 2,2-bis(p-methoxyphenyl)-4-isopropylidenecyclobutanone (2), whereas 2 affords a CA adduct (4), suggesting that a novel rearrangement of 1 to give 2 occurs irreversibly via a radical cation intermediate of 3, a radical cation variant of an unprecedented oxa-analog of tetramethyleneethane.
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© 2003 by Symposium on Fundamental Organic Chemistry
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