1997/12/01 by Anthony J. Arduengo, Frederic M. Davidson, H. V. Rasika Dias +4 · 3 citations
Chemistry · #N-Heterocyclic Carbenes in Organic and Inorganic Chemistry #Cyclopropane Reaction Mechanisms #Catalytic C–H Functionalization Methods #Carbene #Dichlorocarbene #Chemistry #Carbon tetrachloride #Chloroform #Photochemistry #Polymer chemistry #Catalysis #Organic chemistry
paper · doi:10.1021/ja973241o
openalex publication_date 1997/12/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/22
The air-stable crystalline carbene 1,3-dimesityl-4,5-dichloroimidazol-2-ylidene ( 2 ) is produced from the chlorination of 1,3-dimesityimidazol-2-ylidene ( 1 ) by 2 equiv of carbon tetrachloride. The physical and spectroscopic properties of the carbene are reported. The features which contribute to the exceptional stability of the carbene are discussed. Further reaction of 2 with carbon tetrachloride leads to reduction of CCl 4 to dichlorocarbene. The formation of the mixed carbene “dimers” (olefins) from in situ generated dichlorocarbene and various imidazol(in)-2-ylidenes is also reported. The tellurones derived from 1 and 2 are synthesized and compared.