Journal
TETRAHEDRON LETTERS
Volume 46, Issue 12, Pages 2141-2145Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.01.106
Keywords
CO2-carriers; carboxylates; carbonates; ionic liquids
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1,3-Dialkylimidazolium-2-carboxylate compounds have recently been fully characterised. Here we describe the utilisation of 1,3-dimethyl (1a) and 1-butyl-3-methyl-imidazolium-2-carboxylate (1b) in a carboxylation reaction with transfer of the CO2 moiety to benzoylacetone and methanol for the synthesis, in high yield, of benzoylacetate and monoalkylcarbonate anions, respectively. Conversely, when compounds 1a and b are reacted with carbonylic substrates lacking C-H active bonds, a product resulting from nucleophilic attack of the 1,3-dialkylimidazol-2-ylidene species on the carbonyl moiety is obtained. The reported reactions can find applications in organic synthesis and in the synthesis of halogen-free ionic liquids. (C) 2005 Elsevier Ltd. All rights reserved.
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