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Ketonitrones via Cope-Type Hydroamination of Allenes

Joseph Moran, Jennifer Y. Pfeiffer, Serge I. Gorelsky and André M. Beauchemin*

*Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5, Email:

J. Moran, J. Y. Pfeiffer, S. I. Gorelsky, A. M. Beauchemin, Org. Lett., 2009, 11, 1895-1898.

DOI: 10.1021/ol900292r (free Supporting Information)


The reaction of N-alkylhydroxylamines and aqueous hydroxylamine with monosubstituted allenes gives nitrones and oximes, respectively, in good yields. DFT calculations support a proposed concerted, five-membered Cope-type hydroamination process, and calculated transition state energies are in excellent agreement with experimental observations.

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proposed mechanism

Key Words

Nitrones, Oximes

ID: J54-Y2009-1380