Synthesis of 2, 3 fatty aziridines

A new route for the synthesis of 2,3‐aziridines is described. The reaction of methyl 2,3‐dibromohexadecanoate (II) with ammonia at 0 C gave methyl 2‐bromohexadec‐2‐enoate (III, ca. 93%). Compound III, on further treatment with ammonia at 25 C, gave methyl 2‐aminohexadec‐2‐enoate (IV, ca. 5%), methyl trans ‐2,3‐epiminohexadecanoate (V, ca. 64%), methyl cis ‐2,3‐epiminohexadecanoate (VI, ca 24%) and trans ‐2,3‐epiminohexadecamide (VII, ca 3%). The structures were established with the help of elemental analyses and infrared (IR), nuclear magnetic resonance (NMR) and mass spectral analyses.