Transformation of cyclic ketimines to oxaziridines and nitrones
Treatment of 5-, 6- and 7-membered cyclic ketimines bearing alkyl or aryl group with m-chloroperbenzoic acid proceeds as C=N epoxidation and affords bicyclic oxaziridines in good yields, whose subsequent rearrangement gives nitrones.
Voznesenskaia, Natalia G.,Shmatova, Olga I.,Nenajdenko, Valentine G.
Metal-Free Solvent Promoted Oxidation of Benzylic Secondary Amines to Nitrones with H2O2
An environmentally benign protocol for the generation of nitrones from benzylic secondary amines via catalyst-free oxidation of secondary amines using H2O2 in MeOH or CH3CN is described. This methodology provides a selective access to a variety of C-aryl nitrones in yields of 60 to 93%. Several studies have been performed to shed light on the reaction mechanism and the role of the solvent.
Adrio, Javier,Amarante, Giovanni Wilson,Granato, álisson Silva
p. 13817 - 13823
(2021/10/01)
Rearrangements of bicyclic nitrones to lactams: Comparison of photochemical and modified barton conditions
The rearrangement of nitrones to lactams can be carried out by photochemical activation or by treatment with Tf2O followed by KOH-promoted rearrangement (a modification of conditions originally introduced by Barton). Substrates in which the nit
Regiochemistry of mercury(II) oxide oxidation of unsymmetrical N,N-disubstituted hydroxylamines
Mercury(II) oxide oxidation of N,N-disubstituted hydroxylamines with the α and α' carbon atoms containing one and two hydrogen atoms, respectively, gave aldonitrones in a highly regioselective manner. Removal of the α proton is involved in the rate determining step as shown by primary kinetic isotope effect.
Ali, Sk. Asrof,Hashmi, S. M. Azhar,Siddiqui, Mohammad N.,Wazeer, Mohammed I. M.
p. 14917 - 14928
(2007/10/03)
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