The Synthesis and Reactions of Some l-(Nitroaryl)diaziridines

1-(2,4-Dinitrophenyl)- and l-(2,4,6-trinitrophenyl)diaziridines are prepared by treating appropriate diaziridines with 2,4-dinitrofluorobenzene and 2,4,6-trinitroanisole, respectively. The l-(2,4-dinitrophenyl)-3,3-dialkyl- and l-(2,4,6-trinitrophenyl)-3,3-dialkyldiaziridines are isomerized in refluxing toluene into 2,4-dinitrophenyl- and 2,4,6-trinitrophenylhydrazones. However, l-(2,4-dinitrophenyl)-2,3-dialkyldiaziridines and l-(2,4-dinitrophen)rl)-2,3,3-trialkyldiaziridmes are converted in refluxing toluene into 2-alkyl-6-nitrobenzotriazole 1-oxides and ketones. Acid hydrolysis of the l-(nitroaryl)-2-alkyldiaziridines forms l-nitroaryl-2-alkylhydrazines.