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

ABSTRACT: 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 [(PPh₃)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 BPh₃ adducts.

SUBMITTER: Freese T

PROVIDER: S-EPMC9060589 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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

Freese Tyll T Namyslo Jan C JC Nieger Martin M Schmidt Andreas A

RSC advances 20190206 9

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<sub>3</sub>)Au-S-sydnone imine] and a bis(ligand) mercury(ii) complex. The latter possesses a tetrahedral coordinatio ...[more]

PMID: 35514659

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