Chimie des peroxydes en milieu basique I - oxydation des bases de schiff en oxaziridines avec le peroxyde d'hydrogene et un nitrile

An Environmentally Friendly Oxidation System for the Selective Oxygenation of Aldimines to Oxaziridines with Anhydrous TBHP and Alumina‐Supported MoO3 as a Recyclable Heterogeneous Catalyst

“…[2] Oxygenation of imines is an important synthetic transformation as oxaziridines are synthetically important building blocks that find wide application in asymmetric synthesis, [3][4][5] in the preparation of biologically active compounds [6,7] and extensively used as nitrogen [8,9] and oxygen [10,11] transfer reagents in various synthetically important reactions. A variety of oxidizing agents such as m-CPBA, [12][13][14][15][16] Ac 2 O/H 2 O 2 , [17] urea/H 2 O 2 , [18] H 2 O 2 /nitrile, [19,20] tert-amyl hydroperoxide [21] and molecular oxygen [22,23] in the presence of transition metals were used to accomplish this transformation. However, most of these methods are associated with drawbacks such as harsh reaction conditions, the use of aldehydes as a sacrificial agent, the formation of side products, poor yields and difficult work up procedures, which leaves room to develop an efficient and simple process for the oxygenation of imines to oxaziridines.…”

Synthesis of oxaziridines by oxidation of imines with the trichloroacetonitrile–hydrogen peroxide system

“…The photoisomerization of nitrones [15], the electrophilic amination of carbonyl compounds [16] and the oxidation of imines with several oxidizing agents such as buffered oxone ® [8], UHP/maleic anhydride system [17], molecular oxygen in the presence of transition-metal complexes [18] and a nitrile/hydrogen peroxide system [19] have been used for this purpose. Until now, the sole general method, able to lead to oxaziridines 1, 2 and 3, is the oxidation of an imine with a peracid such as m-chloroperbenzoic acid 5 (MCPBA) [8,14,20] (Fig.…”

Stereospecific Synthesis of 2-Alkyl-3-Aryloxaziridines From Prochiral and Chiral N-Arylidenealkylamines by Use of the Benzonitrile-Hydrogen Peroxide System

“…We have found that commercial aqueous hydrogen peroxide of moderate concentration 35% can be used successfully instead of 70% (18) solution to prepare oxaziridines 2a-h. We have found that commercial aqueous hydrogen peroxide of moderate concentration 35% can be used successfully instead of 70% (18) solution to prepare oxaziridines 2a-h.…”