HYDROXY-, ALKOXY-, AMINOMETHYLATION OF NH-OXAZIRIDINES

Article abstract of DOI:10.1007/BF00475333

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 eter 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.