Abstract
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 decreasing pKBH + value of the amine. The role of pH is related to the conditions for the generation of an immonium from the intermediateα-aminocarbinol. The nuclear Overhauser effect was used to determine the orientation of the substituents in several diastereomers of the didikyldiaziridines obtained.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2861–2871, December, 1991.
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Kuznetsov, V.V., Makhova, N.N., Strelenko, Y.A. et al. The role of pH in the synthesis of diaziridines. Russ Chem Bull 40, 2496–2505 (1991). https://doi.org/10.1007/BF00959732
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DOI: https://doi.org/10.1007/BF00959732