Aziridines reaction with acid anhydride

Additionally, Wu and co-workers have shown regioselective ring-opening of aziridines with acid anhydrides mediated by imidiazolinylidene 3 [157]. This pathway requires the use of an electron withdrawing tosylated aziridine 310 in order for the reaction to proceed. The mild reaction conditions allow for a variety of products to be formed in high yields (Table 25). 

Sun X, Ye S, Wu J (2006) A-Heterocyclic carbene an efficient catalyst for the ring-opening reaction of aziridine with acid anhydride. Eur J Org Chem 2006(21 ) 4787 1790... 

Sato et al. observed that the reaction of 2-phenyl-1-azirine with acid chlorides and anhydrides in the presence of triethylamine gives the oxazole directly.57 They have reported that azirines also react with carboxylic anhydrides to give oxazoles (136).57 Aziridine (135) is suggested as a likely intermediate in the reaction of acetic anhydride with azirine (42a), since carrying out the reaction at lower temperature and for a shorter reaction time gave a compound to which they assigned structure 135. 

The anhydride of nitric acid, N20, reacts with 2-methyl aziridine to give the dinitrate (105). In the case of A/-substituted aziridines, the reaction stops at the stage of the nitramine nitrate prior to elimination of N2O (106). 

---