alexa Electron-transfer-induced intermolecular [2+2] cycloaddition reactions based on the aromatic "redox tag" strategy.


Organic Chemistry: Current Research

Author(s): Okada Y, Nishimoto A, Akaba R, Chiba K

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Abstract Novel electron-transfer-induced intermolecular [2+2] cycloaddition reactions between an aliphatic cyclic enol ether and several unactivated olefins have been demonstrated on the basis of the aromatic "redox tag" strategy. The aromatic "redox tag" was oxidized during the formation of the cyclobutane ring, affording the relatively long-lived aromatic radical cation, which was then reduced to complete the overall reaction that constructed the corresponding [2+2] cycloadducts. The aromatic "redox tag" was also found to facilitate electron-transfer-induced cycloreversion reactions of cyclobutane rings. © 2011 American Chemical Society This article was published in J Org Chem and referenced in Organic Chemistry: Current Research

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