Abstract
2, 4-Dinitrobenzenesulfenylnitrene (A) was produced by the oxidation of 2, 4-dinitrobenzenesulfenamide (1) with N-bromosuccinimide, and trapped as N-sulfenylaziridines (3-7). In the presence of a large excess of olefins, the aziridines were produced in 6-57% yields. On the other, when a large excess of 1 was used, the aziridines were synthesized in 62-72% yields based on the olefins. cis-Stilbene gave a mixture of cis-1-(2, 4-dinitrobenzenesulfenyl)-2, 3-diphenylaziridine (8) and the trans isomer (4). On the other hand, trans-stilbene gave only 4. These results suggest the involvement of a biradical intermediate in these reactions.
