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Synthesis of nitrones

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Simple thermal conditions, previously found to minimize hydroxylamine decomposition (t-BuOH, 110 °C), allow the condensation of ketones and hydroxylamines to form exocyclic, acyclic, and α,β-unsaturated ketonitrones with benzylic, linear, and branched nitrogen substituents in modest to excellent isolated.
J. Y. Pfeiffer A. M. Beauchemin, J. Org. Chem., 2009, 74, 8381-8383.


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


A general, efficient and metal-free protocol for the direct oxidation of secondary amines to nitrones tolerates other functional groups or existing stereogenic centers using Oxone in a biphasic basic medium as the sole oxidant.
C. Gella, È. Ferrer, R. Alibés, F. Busqué, P. de March, M. Figueredo, J. Font, J. Org. Chem., 2009, 74, 6365-6367.


Oxidations of organic substrates such as sulfides, secondary amines, N-hydroxylamines, and tertiary amines with molecular oxygen in the presence of 5-ethyl-3-methyllumiflavinium perchlorate catalyst and hydrazine monohydrate in 2,2,2-trifluoroethanol occur highly efficiently to give the corresponding oxidized compounds in excellent yields.
Y. Imada, H. Iida, S. Ono, S.-I. Murahashi, J. Am. Chem. Soc., 2003, 125, 2868-2869.