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Updated: Jul 17, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Intermolecular electrophilic O-amination of alcohols
Alfred Hassner1, Guy Patchornik, Tarun K Pradhan
1Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel. hassna@mail.biu.ac.il
Abstract:
We report the first examples of an intermolecular electrophilic O-amination of aliphatic alcohols. Thus, the new reagents, fluorenone oxime tosylate, 5a, or mesylate, 5b, permit O-amination of diverse alcohols in the presence of NaH under mild conditions. By following the formation of the resulting oxime ethers, 6, the reaction was shown to be sensitive to steric effects in the alcohol. Furthermore, the presence of an aromatic ring or of a double bond in the alcohol molecule (benzyl, allyl) was found to increase the reaction rate.
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