Non-occurrence of a Zincke-like process upon treatment of 1-(2,4-dinitrophenyl)-3-methylimidazolium chloride with a chiral primary amine

Abstract

Huang's preparation of chiral imidazolium salts by means of a Zincke-like process was re-investigated. It was shown that treatment of 1-(2,4-dinitrophenyl)-3-methylimidazolium chloride with L-alaninol gives rise to complete decomposition of the starting salt via an S_NAr reaction and that the material described by Huang was not the claimed chiral imidazolium salt, thus questioning the occurrence of the ionic liquids reported in the original work.