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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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N-heterocyclic carbene coordinated neutral and cationic heavier cyclopropylidenes.

TL;DR: The synthesis and characterization of NHC-coordinated heavier cyclopropylidenes (Si2GeR3X, and Si3R3Br; X=Cl, Mes; R=Tip=2,4,6-iPr3C6H2) in which the three-membered ring is exclusively formed by silicon and germanium are reported.
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An isolable NHC-stabilized silylene radical cation: synthesis and structural characterization.

TL;DR: The silyl-substituted silylene-NHC complex bis(tri-tert-butylsilyl)silylene-(1,3,4,5-tetramethylimidazol-2-ylidene) was synthesized and isolated as air- and moisture-sensitive orange crystals and structurally characterized by X-ray crystallography and electron paramagnetic resonance spectroscopy.
Journal ArticleDOI

A New Class of Organosuperbases, N‐Alkyl‐ and N‐Aryl‐1,3‐dialkyl‐4,5‐dimethylimidazol‐2‐ylidene Amines: Synthesis, Structure, pKBH+ Measurements, and Properties

TL;DR: A series of stable organosuperbases were efficiently synthesized from N,N'-dialkylthioureas and 3-hydroxy-2-butanone and their basicities were measured in acetonitrile and the derivatives with tert-alkyl groups on the imino nitrogen were found to be more basic than the tBuP(1) (pyrr) phosphazene base in aconetitrile.
Journal ArticleDOI

Synthesis and structural characterization of cationic rhenium(V) and technetium(V) dioxo complexes containing four N-heterocyclic carbene ligands.

TL;DR: Cationic dioxorhenium and dioxotechnetium complexes of the composition [MO(2)(L(1))(4)](+) (L( 1) = 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene) have been prepared from various starting materials and studied spectroscopically and by X-ray crystallography.
Journal ArticleDOI

Reactions of the Aluminum(I) Monomer LAl [L = HC{(CMe)(NAr)}2; Ar = 2,6‐iPr2C6H3] with Imidazol‐2‐ylidene and Diphenyldiazomethane. A Hydrogen Transfer from the L Ligand to the Central Aluminum Atom and Formation of the Diiminylaluminum Compound LAl(N=CPh2)2

TL;DR: The solid-state reaction of LAl and imidazol-2-ylidene at elevated temperature (120 °C) yielded the aluminum monohydride N-heterocyclic carbene adduct [{HC[C(CH2)NAr] (CMeNAr)}AlH-{CN(R)C2Me2N(R)}] [R = iPr (1), Me (2)] as mentioned in this paper.
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