Stereoselective trans-N-chlorination of the potassium salt of aziridine-2,2-dicarboxylic acid methyl ester

Primarily trans-1-chloroaziridine is formed in the chlorination of the potassium salt of aziridine-2,2-dicarboxylic acid methyl ester. The silver salt and then the mixed methyl ethyl ester, as well as the trimethylammonium and α-phenylethylammonium salts, were obtained from trans-1-chloroaziridine. Signals of diastereomers are observed in the PMR spectrum of the E isomer of the α-phenylethylammonium salt; this opens up the fundamental possibility of separation into antipodes.