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

Green Chemistry Pub Date: 2008-07-14 DOI: 10.1039/B804650F

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 SNAr 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.

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