The nitrenes (II), generated by thermolysis of the azides (I), react with the monosubstituted benzenes (III), producing the p‐ or o‐phenylated isoureas (IV) and (V).
Aziridines are very important precursors to a wide range of biologically active molecules such as amino acids, antibiotics, alkaloids, and many others. 1 The two most important aspects of this class of compounds have been the stereo-regio-selectivity of their synthesis and energy barrier of nitrogen inversion. 1-3 Both aspects have very important effects on their physical and/or chemical behaviours. Lwowski and co-workers reported a highly stereoselective synthesis of aziridines via a reaction of imidoyl nitrene with olefines. 4 Dabbagh and coworkers reported that certain imidoyl nitrenes are known to have moderate reactivity with higher selectivity. 5,6 Recently, Atkinson and co-workers have described the preparation of range of aziridines via reagent-controlled diastereoselective aziridination of alkenes using 3-acetoxyaminoquinazolinones. 7 They further reported the acid-catalysed aziridine ring-opening with retention of configuration. Furthermore, the interconversion of the isomers on nitrogen of nitrogen-containing organic compounds has been the cornerstone of research interests for the last half century. 2,8 Generally, the rapid nitrogen inversion of ordinary amines focused the attention on aziridine with its much lower inversion rate, because of strain in the three member ring. 2,9 The aziridines' nitrogen inversion has been investigated in detail. 2,3,9
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