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

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Freese , T , Namyslo , J C , Nieger , M & Schmidt , A 2019 , ' Sulfur, mercury, and boron adducts of sydnone imine derived anionic N-heterocyclic carbenes ' , RSC Advances , vol. 9 , no. 9 , pp. 4781-4788 . https://doi.org/10.1039/c9ra00294d

Title: Sulfur, mercury, and boron adducts of sydnone imine derived anionic N-heterocyclic carbenes
Author: Freese, Tyll; Namyslo, Jan C.; Nieger, Martin; Schmidt, Andreas
Contributor: University of Helsinki, Department of Chemistry
Date: 2019-02-11
Language: eng
Number of pages: 8
Belongs to series: RSC Advances
ISSN: 2046-2069
URI: http://hdl.handle.net/10138/300100
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.
Subject: CONJUGATED MESOMERIC BETAINES
NUCLEOPHILIC CARBENES
COMPLEXES
IMIDAZOL(IN)IUM-2-CARBOXYLATES
PRECURSORS
CHEMISTRY
PALLADIUM
INDAZOLE
YLIDES
DFT
116 Chemical sciences
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