The role of pH in the synthesis of diaziridines 2. The effect of pH on the synthesis of diaziridines from amines, carbonyl compounds and NaOCl

In the synthesis of diaziridines from amines, carbonyl compounds, and NaOCl in water, the yields of 1,2-dialkyldiaziridines and of 1,2,3-trisubstituted diaziridines prepared from amines with electron-withdrawing substituents in the side chain are less sensitive to changes in pH than the yields of 1,2,3-trialkyldiaziridines with simple alkyl substituents. The formation of 1,5-diazabicyclo[3.1.0]hexanes is insensitive to the pH in 6.5–13.0 range. This difference is explained by the occurrence of two competing pathways to the key intermediate,N-chloroaminal.