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-tri substituted diaziridines prepared from amines with electron-withdrawin g subsituents in the side chain are less sensitive to changes in pH th an the yields of 1,2,3-trialkyldiaziridines with simple alkyl substitu ents. The formation of 1,5-diazabicyclo[3.1.0]hexanes is insensitive t o the pH in 6.5-13.0 range. This difference is explained by the occurr ence of two competing pathways to the key intermediate, N-chloroaminal .