IODINE-CATALYZED AZIRIDINATION OF ALKENES USING CHLORAMINE-T AS A NITROGEN-SOURCE

Iodine was found to be an efficient catalyst for the aziridination of alkenes utilizing Chloramine-T (N-chloro-N-sodio-p-toluenesulfonamide) as a nitrogen source. For example, when two equivalents of styrene we re added to Chloramine-T in the presence of a catalytic amount of iodi ne in a 1 : 1 solvent mixture of acetonitrile and neutral buffer, the corresponding aziridine 1 was obtained in 91% yield. The reaction coul d be applied to other acyclic and cyclic alkenes such as 1-octene and cyclohexene. The aziridination of p-substituted styrene derivatives 2- 5 with Chloramine-T showed that electron-rich alkenes reacted faster t han electron-poor ones. Several Chloramine-T analogs were also examine d and were found to give the corresponding aziridines 8-10 in only mod erate yields. (C) 1998 Elsevier Science Ltd. All rights reserved.