THE ROLE OF pH IN THE SYNTHESIS OF DIAZIRIDINES

Article abstract of DOI:10.1007/BF00959732

The greatest yield in the synthesis of diaziridines from carbonyl compounds, amines, and aminating reagents in water is achieved at a specific pH, which shifts to less alkaline values with increasing -I effect of the substituents in the carbonyl compound and with increasing pK_BH+ value of the amine.The role of pH is related to the conditions for the generation of an immonium from the intermediate α-aminocarbinol.The nuclear Overhauser effect was used to determine the orientation of the substituents in several diastereomers of the dialkyldiaziridines obtained.