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 organization: | Department of Chemistry |
Date: | 2019-02-11 |
Language: | eng |
Number of pages: | 8 |
Belongs to series: | RSC Advances |
ISSN: | 2046-2069 |
DOI: | https://doi.org/10.1039/c9ra00294d |
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 |
Peer reviewed: | Yes |
Rights: | cc_by |
Usage restriction: | openAccess |
Self-archived version: | publishedVersion |
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