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Cover Picture: Cycloelimination of Imidazolidin‐2‐ylidene N‐Heterocyclic Carbenes: Mechanism and Insights into the Synthesis of Stable “NHC‐CDI” Amidinates (Chem. Eur. J. 15/2015)
Author(s) -
Zhukhovitskiy Aleksandr V.,
Geng Julie,
Johnson Jeremiah A.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201590057
Subject(s) - carbodiimide , chemistry , nucleophile , reagent , aryl , combinatorial chemistry , organic chemistry , catalysis , alkyl
Bis(aryl)imidazolidin‐2‐ylidene N‐heterocyclic carbenes (NHCs) undergo quantitative conversion to zwitterionic amidinates upon heating. This transformation involves a [3+2] cycloelimination of the NHC to generate ethylene and a carbodiimide, the latter is immediately trapped by a second NHC. The unique structures, optical properties, and bench stability of the products of this reaction prompted the synthesis of mixed analogues by direct addition of NHCs to carbodiimides. For more details see the Communication by J. Johnson and co‐workers on page 5685 ff.