1,3-Diaryl-2,2-dihaloaziridines in nitration and bromination reactions

In the nitration of 3-(4-nitrophenyl)-1-phenyl-2,2-dichloroaziridine in acetic acid, 1-(o- and p-nitrophenyl)-derivatives are formed in a 35:65 ratio. 1,3-Di-phenyl-2,2-dichloroaziridine undergoes opening of the three-membered ring under the same conditions, forming a mixture of o- and p-nitroanilides and 2-nitro-4-chloroanilides of 2-acetoxy (or 2-chloro)-2-phenylacetic acids. The bromination of 3-(4-nitrophenyl)-1-phenyl-2,2-dichloroaziridine in aqueous acetic acid leads to 1-(4-bromophenyl)-3-(4-nitrophenyl)-2,2-dichloroaziridine, while in a mixture of acetic acid and acetic anhydride it leads to the anilide of 2-bromo-2-phenyl-acetic acid and 2-bromo-N-(2,4-dibromophenyl)-1-(4-nitrophenyl)-2,2-dichloro-ethylamine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 912–916, July, 1984.