Sulfur, mercury, and boron adducts of sydnone imine derived anionic N-heterocyclic carbenes

The sydnone imines (5-benzoylimino)-3-(2-methoxyphenyl)-sydnone imine and molsidomine were deprotonated at C4 to give sydnone imine anions which can be represented as anionic N-heterocyclic carbenes, respectively. Trapping reactions with sulfur gave unstable sydnone imine sulfides which were stabilized by the formation of methyl thioethers, methyl sulfoxides, gold complexes [(PPh(3))Au–S-sydnone imine] and a bis(ligand) mercury(ii) complex. The latter possesses a tetrahedral coordination of the mercury central atom to the sulfur atoms with the N6 nitrogen atoms coordinating as neutral ligands. Water converted the molsidomine anion into ethyl(2-morpholino-2-thioxoacetyl)carbamate. Mercury(ii)chloride and triphenylborane were employed to trap the sydnone imine carbenes as mercury complexes as well as BPh(3) adducts.