Synthèse et réactivité des halogéno-2 sulfonyl-2 aziridines

Abstract

Carbon tetrahalide reacts rapidly with 2-phenylsulfonyl aziridines in the presence of KOH, leading to 2-phenylsulfonyl 2-haloaziridines.Starting with 2-isopropylsulfonyl aziridines, a monochloro and a dichloroaziridine are produced; the Ramberg–Bäcklund reaction is not observed.These halo compounds decompose either thermally or in acidic medium leading to N-substituted α-haloacetamides and α-phenylsulfonylacetamides. 2-Phenylsulfonyl 2-haloaziridines are unreactive toward potassium cyanide or sodium thiophenoxide. Sodium methoxide, sodium ethoxide, or sodium thioethoxide reduce them to 2-phenylsulfonyl aziridines; the reaction depends upon the solvent.