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G. Steiner, A. Krajete, H. Kopacka, K.-H. Ongania, K. Wurst, P. Preishuber-Pflügl and B.Bildstein, “[1,2]-Rear- rangement of Imino-N-heterocyclic Carbenes—Synth- esis and Structures of Chelating Iminoimidazole Pd and Ni Complexes,” European Journal of Inorganic Chem- istry, Vol. 2004, No. 14, 2004, pp. 2827-2836.
doi:10.1002/ejic.200400070
has been cited by the following article:
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TITLE:
Investigation of the Role of Electrogenerated N-Heterocyclic Carbene in the Staudinger Synthesis in Ionic Liquid
AUTHORS:
Marta Feroci
KEYWORDS:
Electrosynthesis, NHC, Staudinger Synthesis, ?-Lactams, Organocatalyst, Ionic Liquid
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.1 No.4,
December
27,
2011
ABSTRACT: Electrogenerated N-heterocyclic carbene (NHC), obtained by cathodic reduction of Bmim-BF4, behaves as organocatalyst and base in the Staudinger synthesis from an acyl chloride and a deactivated imine in ionic liquid to yield ?-lactams. The effect of many parameters (temperature, amount of electricity, substituents, presence of an external base) has been evaluated and a tentative mechanism for the Staudinger synthesis in a very polar medium like the ionic liquid reported. The yields of isolated ?-lactams are good, starting from non-electrophilic imines, and predominantly trans lactams are obtained with a good diastereomeric ratio.