Bulletin of the Academy of Sciences of the USSR Division of Chemical Science p. 2496 - 2505 (1991)
Update date:2022-09-26
Topics: pH Control
Kuznetsov, V. V.
Makhova, N. N.
Strelenko, Yu. A.
Khmel'nitskii, L. I.
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 pKBH+ 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.
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