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Issue 9, 2019, Issue in Progress

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

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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.

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

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Article information


Submitted
12 Jan 2019
Accepted
31 Jan 2019
First published
06 Feb 2019

This article is Open Access

RSC Adv., 2019,9, 4781-4788
Article type
Paper

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

T. Freese, J. C. Namyslo, M. Nieger and A. Schmidt, RSC Adv., 2019, 9, 4781 DOI: 10.1039/C9RA00294D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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