The stereoselective synthesis and the nitrogen interconversion studies of 2-(tert-butoxymethyl)-1-[N'-(4-methylbenzenesulfonyl) (4-methylphenoxy) imidoyl] aziridine

Abstract

One-pot synthesis of the title compound (1) is achieved from tert-butyl allyl ether (2) and the N'(4-methylbenzenesulfonyl) (4-methylphenoxy) imidoyl azide (3) in high yield. The energy barrier of nitrogen interconversion of the title compound (1) was investigated by dynamic NMR. The free energies of activation (ΔG(+)) are 11.11 kcal/mol (T(c) = 238 K) and 11.30 kcal/mol (T(c) = 242 K) in acetone-d6 and chloroform-d, respectively, and are attributed to nitrogen inversion of aziridine ring nitrogen.