Imidazolium compounds have determined a profound impact on chemistry, and several synthetic methods to access them are well established. Here, we report the serendipitous discovery of the unprecedented route to a zwitterionic imidazolium molecule with the two nitrogen atoms substituted with 4-cyclohexanecarboxylic acid: to build the five-membered ring, glyoxal plays the double role of source for C2 and, unusually, C1 units, the latter via thermal decomposition affording carbon monoxide as side-product. Compound I1 was characterized by elemental analysis, multinuclear NMR, IR and ESI-MS spectroscopy.

Serendipitous Formation of a Zwitterionic Imidazolium Molecule from α-Diimine with Glyoxal as Unusual Cyclization Agent

Biancalana L.
Primo
;
Bresciani G.;Marchetti F.;
2021-01-01

Abstract

Imidazolium compounds have determined a profound impact on chemistry, and several synthetic methods to access them are well established. Here, we report the serendipitous discovery of the unprecedented route to a zwitterionic imidazolium molecule with the two nitrogen atoms substituted with 4-cyclohexanecarboxylic acid: to build the five-membered ring, glyoxal plays the double role of source for C2 and, unusually, C1 units, the latter via thermal decomposition affording carbon monoxide as side-product. Compound I1 was characterized by elemental analysis, multinuclear NMR, IR and ESI-MS spectroscopy.
2021
Biancalana, L.; Bresciani, G.; Marchetti, F.; Pampaloni, G.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/1119425
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