Metal-free intramolecular aziridination of alkenes using hypervalent iodine based sulfonyliminoiodanes.

Intramolecular aziridination of alkenyl sulfonyliminoiodanes occurs thermally in the absence of conventional metal catalysts such as Rh(II) and Cu(II). In rigid molecular systems, conversions are near quantitative. The scope of the nonmetal process is related to the conformational flexibility of the alkenyl sulfonyliminoiodane. A mechanism is proposed involving formal 2 + 2 cycloaddition of the RSO(2)N=IPh group to the double bond followed by reductive elimination of PhI to yield the sulfonylaziridine. Green chemistry aspects of the process are highlighted.