We thank the Deutsche Forschungsgemeinschaft (SFB 749, project B1) for financial support, Dr. P. Mayer for the determination of the X-ray structures, and Dr. K. Troshin, Dr. D. S. Stephenson, Dr. J. Ammer, Dr. A. R. Ofial, and the members of COST action CM0905 “Organocatalysis” for helpful discussions. We are grateful to Prof. L. Delaude (Univ. Liége) for kindly providing a preprint of Ref. [12c].
Structures and Ambident Reactivities of Azolium Enolates†
Article first published online: 29 JUL 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 42, pages 11163–11167, October 11, 2013
How to Cite
Maji, B. and Mayr, H. (2013), Structures and Ambident Reactivities of Azolium Enolates. Angew. Chem. Int. Ed., 52: 11163–11167. doi: 10.1002/anie.201303524
- Issue published online: 10 OCT 2013
- Article first published online: 29 JUL 2013
- Manuscript Revised: 15 MAY 2013
- Manuscript Received: 25 APR 2013
- Deutsche Forschungsgemeinschaft
- acylazolium ions;
- N-heterocyclic carbenes;
Oxygen versus carbon: Azolium enolates were generated by the reactions of N-heterocyclic carbenes (NHCs) with methyl phenyl ketene and characterized by X-ray crystallography. Kinetic studies show that the enolate oxygen is 20 times more nucleophilic than the carbon atom, but under thermodynamic control exclusive C-addition products were formed.