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Nitrosobenzene-Mediated C-C Bond Cleavage Reactions and Spectral Observation of an Oxazetidin-4-one Ring System

Joshua N. Payette and Hisashi Yamamoto*

*Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, Email:

J. N. Payette, H. Yamamoto, J. Am. Chem. Soc., 2008, 130, 12276-12278.

DOI: 10.1021/ja804325f

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A transition-metal-free oxidative C-C bond cleavage process for a broad range of ester and dicarbonyl compounds involves carbanion addition to nitrosobenzene and proceeds via fragmentation of a previously unobserved oxazetidin-4-one heterocycle.

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Key Words

ketones, imines, α-keto carboxylic esters, nitrosobenzene

ID: J48-Y2008-2520