Abstract
3,3-Dimethyloxaziridine reacts with chloral and acetaldehyde to give crystalline N-(α-hydroxyalkyl)oxaziridines; the reaction with acetaldehyde is reversible. The N-aminomethylation of NH-oxaziridines is not realized, evidently because of the tendency of oxaziridines to iminate nucleophiles. The weakly nucleophilic chloromethylphthalimide and chloromethyl methyl ether give imidomethyl- and methoxymethyloxaziridines. 3,3-Dimethyldiaziridine reacts with excess chloromethyl methyl ether to give the N-monomethoxymethyl derivative. It is shown that α-hydroxyalkyloxaziridines and methoxymethyl-substituted oxaziridine and dizaridine do not enter into the aminomethylation of compounds with a labile hydrogen.
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Communication 54 of the series “Asymmetric Nitrogen” (see [1] for communication 53); communication 35 of the series “Geminal Systems” (see [2] for communications 34).
Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 24, No. 3, pp. 390–395, March, 1988.
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Varlamov, S.V., Kadorkina, G.K. & Kostyanovskii, R.G. Hydroxy-, alkoxy-, aminomethylation of NH-oxaziridines. Chem Heterocycl Compd 24, 320–325 (1988). https://doi.org/10.1007/BF00475333
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DOI: https://doi.org/10.1007/BF00475333