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Journal ArticleDOI

Synthesis of Imidazol-2-ylidenes by Reduction of Imidazole-2(3H)-thiones

Norbert Kuhn, +1 more
- 01 Jan 1993 - 
- Vol. 1993, Iss: 06, pp 561-562
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TLDR
In this article, an improved synthesis of the title compounds was reported, and the N,N'-dialkylthioureas 1 with 3-hydroxy-2-butanone gave the imidazole-2(3H)-thiones 2 which on treatment with potassium in boiling tetrahydrofuran give the IMidazol-2ylidenes 3 in excellent yields
Abstract
An improved synthesis of the title compounds is reported. Reaction of the N,N'-dialkylthioureas 1 with 3-hydroxy-2-butanone gives the imidazole-2(3H)-thiones 2 which on treatment with potassium in boiling tetrahydrofuran give the imidazol-2-ylidenes 3 in excellent yields

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Citations
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Journal ArticleDOI

Preparation of Metal-Imidazolidin-2-ylidene Complexes by Oxidative Addition

TL;DR: An entry into (chiral) palladium complexes bearing N-heterocyclic carbene (NHC) ligands is outlined on the basis of the oxidative addition of Pd(PPh3)4 to easily accessible 2-chloro-1...
Journal ArticleDOI

Diaminocarbenes; Calculation of Barriers to Rotation about Ccarbene−N Bonds, Barriers to Dimerization, Proton Affinities, and 13C NMR Shifts

TL;DR: Barriers to rotation about the Ccarbene−N bonds in diaminocarbene (H2N)2C 1a, bis(dimethylamino)carbene ((CH3)2N)-2C1b, and the related formamidinium ions (H 2N) 2CH+ 2a and ((CH 3)2Ns)-2CH+2b, respectively, have been calculated using density-functional theory in order to study the extent of π-bond stabilization of the carbene center.
Journal ArticleDOI

A Cyclic Diaminocarbene with a Pyramidalized Nitrogen Atom: A Stable N‐Heterocyclic Carbene with Enhanced Electrophilicity

TL;DR: The synthesis and single crystal X-ray diffraction study of a cyclic diaminocarbene is reported, which retains the nucleophilicity of classical NHCs, but displays enhanced electrophilicity.
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