Attempted aziridinations and sulfonilimations using simple iron catalysts and hypervalent iodine reagents

Aziridines and sulfonilimines are among some of the most important functional groups in organic chemistry. We report here our work toward the synthesis of these molecules from alkenes using simple iron catalysts and hypervalent iodine reagents. Alkene, solvent, iron catalyst, hypervalent iodine source, and amide source were varied, but no appreciable amount of aziridine was obtained. The same reaction conditions were attempted for the sulfonilimation of sufide or sulfoxide substrates, and a significant amount of product was obtained. The use of FeCl3 in the reaction does seem to accelerate the formation of product, but oxidation is also seen in the absence of iron catalyst or hypervalent iodine source