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

In the presence of zinc oxide and without any additional organic solvents,
Beckmann rearrangement of several ketones and aldehydes were performed in
good yields.
H. Sharghi, M. Hosseini, Synthesis, 2002, 1057-1059.

A new synthesis of enamides from ketones involves a phosphine-mediated reductive
acylation of oximes. The resulting enamides are isolated in good yields and
excellent purity.
H. Zhao, C. P. Vandenbossche, S. G. Koenig, S. P. Singh, R. P. Bakale, Org. Lett., 2008,
10, 505-507.

J. P. Waldo, R. C. Larock, Org. Lett.,
2005, 7, 5203-5205.

With a simple two-step procedure involving substitution with readily available
TsNHOTBS and subsequent treatment with CsF, a range of oximes were prepared from
the corresponding alcohols, alkyl halides, or alkyl sulfonates without using
external oxidants.
K. Kitahara, T. Toma, J. Shimokawa, T. Fukuyama, Org. Lett., 2008,
10, 2259-2261.

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 number of new reactions of IBX with heteroatom-containing substrates were
discovered and their utility was demonstrated. IBX was used for the generation
of imines from secondary amines in notably high yields, for the oxidative
aromatization of nitrogen heterocycles and for the cleavage of dithianes.
K. C. Nicolaou, C. J. N. Mathison, T. Montagnon, Angew.
Chem., 2003, 115, 4211-4216.

A convenient, environmentally friendly method for the synthesis of optically
active aldoximes and nitriles starting from chiral nitroalkanes was
developed.
C. Czekelius, E. M. Carreira, Angew. Chem. Int. Ed., 2005,
44, 612-615.
