Reaction between 2-phenylaziridines and 3-halogenocyclohex-2-enones

Abstract

The reaction of 2-phenyl- or 2-(3,4-methylenedioxyphenyl)aziridine with 3-chlorocyclohex-2-enone give principally 3-(2-hydroxy-2-phenylethylamino)cyclohex-2-enone or 3-[2-hydroxy-2-(3,4-methylenedioxyphenyl)-ethylamino]cyclohex-2-enone, respectively, instead of the expected aziridines, in each case via the 2-chloro-derivative. 2-Benzyl-3-phenylaziridine and 2-chlorocyclohex-2-enone combine to form the expected 3-aziridinylcyclohex-2-enone, which does not easily undergo ring expansion with iodide ion.