The 2-position of imidazolium ionic liquids: substitution and exchange.
The 2-position of imidazolium cations is known to be relatively acidic, leading to the useful Arduengo-type carbenes. At the same time, the acidity of this site can lead to undesired side reactions when using imidazolium-based ionic liquids as solvents. In this note, we describe the surprisingly facile deuterium exchange at this position and also the synthesis and exchange under modestly basic conditions (triethylamine) of a series of 2-methyl-substituted compounds.
Handy
Scott T
ST
Department of Chemistry, State University of New York at Binghamton, Binghamton, New York 13902, USA. shandy@binghamton.edu
Okello
Maurice
M
D002412:Cations / Q000737:chemistry; D003903:Deuterium / Q000737:chemistry; D041961:Deuterium Exchange Measurement; D005021:Ethylamines / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*
D002412:Cations; D005021:Ethylamines; D007093:Imidazoles; D012997:Solvents; D003903:Deuterium; C016162:triethylamine