Intermolecular electrophilic O-amination of alcohols

Alfred Hassner, Guy Patchornik, Tarun K. Pradhan, R. Kumareswaran

Research output: Contribution to journalArticlepeer-review

10 Scopus citations


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.

Original languageEnglish
Pages (from-to)658-661
Number of pages4
JournalJournal of Organic Chemistry
Issue number2
StatePublished - 19 Jan 2007
Externally publishedYes


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