Intermolecular trapping of sulphenylnitrenes by alkenes

Abstract

Oxidation of 2,4-dinitrobenzenesulphenamide with lead tetra-acetate in the presence of electron-rich alkenes (styrene, (E)- and (Z)-1-phenylpropene, 2-phenylpropene, (Z)-but-2-ene, and butadiene) gives the corresponding substituted N-(2,4-dinitrophenylsulphenyl)aziridines. Intermolecular trapping of a presumed sulphenylnitrene intermediate is also successful in the oxidation of 2-nitrobenzenesulphenamide but fails for RSNH₂ when R = PhCO, 4-ClC₆H₄, or 4-NO₂C₆H₄.