An experimental and computational study of thereactions of singlet oxygen with N-substitutedsulfenamides is reported. Intermediates capable of epoxidizingnorbornene were observed duringthe photooxidations of three sulfenamides. These results are usedto argue for formation ofiminopersulfinic acids. The structural integrity of twoiminopersulfinic acids was supported bytheir successful location at the MP2/6-31G* level of theory.Furthermore, the inability to locatecomputationally significant persulfinimide precursors suggests that theiminopersulfinic acids formby enelike reactions involving near-simultaneous addition of singletoxygen to sulfur and hydrogenabstraction.