PREPARATION AND EVALUATION OF NITRENE PRECURSORS (PHI=NSO2AR) FOR THECOPPER-CATALYZED AZIRIDINATION OF OLEFINS

The preparation of different [N-(arenesulfonyl)imino]phenyliodinanes i s described along with an evaluation of their utility as nitrene precu rsors for the copper-catalyzed aziridination of different olefins. The best results were obtained with p-NO2-C6H4SO2N=IPh and p-MeO-C6H4SO2N =IPh, both of which were found superior to PhI=NTs, which previously h as been the reagent of choice for this type of reaction. The correspon ding aziridine derivatives were obtained in good to excellent yields ( 60-99%) using 1.0 equivalent of olefin and 1.5 equivalents of the nitr ene precursor. (C) 1997 Elsevier Science Ltd.