Categories: C=N Bond Formation >
Synthesis of nitrones
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Recent Literature

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.
