Reaction of an asymmetric imidazolinium compound with nucleophiles

Abstract

1-Methyl-3-(p-nitrophenyl)-2-phenylimidazolinium iodide (2) reacts easily with nucleophiles to give addition products of various stabilities. In sodium hydroxide or a silver oxide suspension compound (2) reacted to give N-benzoyl-N-methyl-N′-(p-nitrophenyl)ethylenediamine (4), the structure of which was confirmed by synthesis from N-(2-bromoethyl)-N-methylbenzamide and p-nitroaniline. Treatment of compound (2) with IRA-400 resin (OH–) afforded the imidazolinium hydroxide which rearranged to (4). Reaction of (2) with sodium methoxide in anhydrous methanol afforded 2-methoxy-1-methyl-3-(p-nitrophenyl)-2-phenylimidazolidine which was hydrolysed readily to (4). Sodium borohydride reduces (2) to 1-methyl-3-(p-nitrophenyl)-2-phenylimidazolidine.