Categories: N=O Bond Formation, N-O Bond Formation >
Synthesis of nitro compounds
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Recent Literature
The high reactivity of ozone and its propensity to overoxidize organic
molecules, including most solvents can largely be mitigated by adsorbing both
substrate and ozone onto silica gel, providing a solvent-free oxidation method.
A flow-based packed bed reactor approach provides exceptional control of
temperature and time for oxidation of amines to nitroalkanes and the synthesis
of pyridine N-oxides.
E. A. Skrotzki, J. K. Vandavasi, S. G. Newman, J. Org. Chem., 2021, 86,
14169-14176.
An efficient cobalt-catalyzed protocol for the selective oxidation of
anilines using a combination of inexpensive tert-butyl hydroperoxide and
Co(OAc)2·4H2O without any ligand provides nitroarene
products in very good yields.
L. Wu, L. Yao, W. Yin, J. Yu, Synthesis, 2023,
55, 3104-3108.
Several primary aromatic amines were converted to their corresponding nitro
compounds in good yields with sodium perborate tetrahydrate (SPB) in
micellar media in the presence of a catalytic amount of tungstophosphoric
acid (H3PW·nH2O).
H. Firouzabadi, N. Iranpoor, K. Amani, Green Chemistry, 2001, 3, 131-132.
The use of nonanebis(peroxoic acid) enables a regio- and chemoselective
oxidation of aromatic amines hindered with an ortho substituent to the
corresponding nitro compounds, except for anilines ortho-substituted with
amino groups (NH2, NHR) or hydroxyl groups, where H-bonding between
an hydrogen of the adjacent group and an oxygen atom from the diperoxy acid
directs the oxidation.
V. V. Patil, G. S. Shankarling, J. Org. Chem.,
2015,
80, 7876-7883.
A convenient oxidation of oximes to nitro compounds uses sodium perborate in
glacial acetic acid as oxidizing agent.
G. A. Olah, P. Ramaiah, C.-S. Lee, G. K. Surya Prakash, Synlett, 1992, 337-339.