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- Title
Cycloelimination of Imidazolidin-2-ylidene N-Heterocyclic Carbenes: Mechanism and Insights into the Synthesis of Stable 'NHC-CDI' Amidinates.
- Authors
Zhukhovitskiy, Aleksandr V.; Geng, Julie; Johnson, Jeremiah A.
- Abstract
We report the discovery that 1,3-bis(aryl)imidazolidin-2-ylidenes, one of the most widely studied classes of N-heterocyclic carbenes (NHCs), undergo quantitative conversion to zwitterionic 'NHC-CDI' amidinates upon heating to ≈100 °C in solution. The mechanism of this novel NHC decomposition process is studied in detail. These studies enabled the rational synthesis of a new class of bench stable amidinates from a panel of NHCs and carbodiimides. We expect these constructs to find utility in a variety of applications.
- Subjects
AMIDINES; HETEROCYCLIC compounds; CYCLOELIMINATION reactions; IMIDAZOLIDINES; CARBENE analogues
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 15, p5685
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201500052