A Facile Deamination of Aziridines Using N₂O₄Under Very Mild Conditions

Dinitrogen Tetroxide: N2O4

“…10 Various aziridines were reacted with dinitrogen tetroxide in the presence of Et 3 N in anhyd THF to give the corresponding ethylenes in good to excellent yields. 11 [60]Fullerene was selectively and efficiently nitrated with dinitrogen tetroxide to yield monodisperse hexanitro[60]fullerene. The use of this compound as reactive precursor in the synthesis of organo-amino derivatives of C 60 was also demonstrated.…”

N-bromosuccinimide/cerium Ammonium Nitrate: An Efficient Reagent for Stereo-controlled Deamination of Ketoaziridines

“…The presence of electron-withdrawing substituents activates the ring, which then reacts easily with nucleophiles to form ring-opened products. Efforts, have been devoted to the development of the reactions of activated' aziridines with different reagents over the past decade, leading to a variety of the products 5,6 In contrast to activated aziridines, non-activated aziridines are relatively inert towards nucleophilic reagents. 7,8 Among the reactions of aziridines, the deamination of aziridines has been attractive for mechanistic, structural, thermodynamic and theoretical reasons.…”

“…Several methods have been described for the deamination of a variety of aziridines. [9][10][11] We have explored different reactions of 2-aroyl-3-aryl aziridines affording functionalised and other valuable N-containing compounds. [12][13][14][15][16][17][18][19][20] In continuation of our research activities in the field of the reactions of aziridines, we have found that N-bromosuccinimide (NBS)/cerium (IV) ammonium nitrate (CAN) is a suitable reagent for deamination of N-H, N-aryl and N-aroyl 2-benzoyl-3-phenyl aziridines.…”

Stereo-controlled Deamination of Ketoaziridines Using Ph3P/I2

“…[9][10][11][12][13][14][15] Among the reactions of aziridines, the deamination of aziridines has been attractive for mechanistic, structural, thermodynamic and theoretical reasons. Several methods have been described for the deamination of a variety of aziridines using some reagents such as N 2 O 4 , 9 N-nitroso-3-nitrocarbazole, 16 nitrosyl chloride, 17 methyl nitrite, 17 n-butyl nitrite 18 and organosilyllithium. 19 However these reagents suffer from at least one of the following disadvantages: (1) high costs of preparations, (2) expensive reagents (3) tedious work-up procedures and (4) nitrosation agents.…”