Heteroatomic derivatives of aziridine

Abstract

The reaction of ethyleneimine with sulfenyl chlorides RSCl at −10‡ C in the presence of a hydrogen chloride acceptor (triethylamine) leads to the formation of N-organylthioaziridines${\text{RS}}{\text{H}}_{\text{2}}$. Compounds with R=n-C₅H₁₁, C₆H₅, o-O₂NC₆H₄ and C₆H₆CH₂ have been obtained by this method.${\text{(CH}}_{\text{3}} {\text{)}}_{\text{3}} {\text{SS}}{\text{H}}_{\text{2}}$ and${\text{(C}}_{\text{2}} {\text{H}}_{\text{5}} {\text{)}}_{\text{2}} {\text{NS}}{\text{H}}_{\text{2}}$. have been synthesized analogously.

The properties and IR spectra of these compounds have been studied. The action of methyl iodide on N-phenylthioaziridine leads to disproportionation of the molecule with the formation of diphenyl disulfide, Β-iodoethyltrimethylammonium iodide, and free iodine.