Abstract
Carbene-mediated transformations of N-(3-butyl-benzimidazol-3-ium-1-yl)-1-arylmethanimine iodides with carbon disulfide and benzoyl isothiocyanate gave the corresponding NHC center dot CS(2) betaines in 68-85% and benzoyl-[1-butyl-3-[(E)-(aryl)-methyleneamino]benzimidazol-1-ium-2-carbothioyl]azanides, respectively, in 74-85% yields. However, reaction with excess isopropyl isothiocyanate in NaH/THF at room temperature yielded the 1-butyl-1',3'-diisopropyl-3-[(E)-(aryl)methyleneamino]spiro[benzimidazole-2,5'-imidazolidine]-2',4'-dithiones (74-77%).