The synthesis of a new N-heterocyclic carbene with bulky S-arylthiocarbamate substituents was devised from the condensation between 2-chloromethyl-4-methy-l,6-[3,5-bis(trifluoromethyl)-phenyl]-S-phenyl-N,N-dimethylthiocarbamate and imidazole, resulting in the proligand N,N’-bis[(2-S-(N’’,N’’-dimethylthiocarbamoyl)-5-methyl)phenylmethyl]imidazolium iodide [H(S-carb)2NHC]I. This newly synthesized proligand was crystallographically characterized, thus confirming its identity; its stability was established in several solvents, resulting in air oxidation in methanolic solution, giving rise to the decomposition product N,N’-bis[(2-S-(N’’,N’’-dimethyl thiocarbamoyl)-5-methyl)phenylmethyl]-4,5-dimethoxyimidazolyl-2-one. Reaction of the proligand with silver oxide afforded the corresponding complex [(S-carb)2NHC]AgI, which was fully characterized by spectroscopic techniques.
Keywords:
carbenes; organic reactions; inorganic synthesis; spectroscopy
