Related Experiment Video
Updated: Jul 1, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Synthesis of Cationic Calcium Amido Complexes via Silylium-Mediated Abstraction Reactions
Lucas Winkler1, Alexander Hinz1,2
1Karlsruhe Institute of Technology (KIT), Institute of Inorganic Chemistry (AOC), Kaiserstr. 12, Karlsruhe 76131, Germany.
Abstract:
The two molecular calcium amides [(dtbpCbz)Ca(thf)N(SiMe3)2] and [(dtbpCbz)CaN(SiMe3)2] (dtbp = 3,5-di-tert-butylphenyl, Cbz = carbazolyl) were reacted with the silylium salt [(Et3Si)2H][B(C6F5)4] in an attempt to facilitate abstraction of the bis(trimethylsilyl)amido ligand. However, abstraction of the silylamide was not observed in either case, and distinct cationic calcium amides were isolated. In the reactions with the tetrahydrofuran-coordinated starting material, the carbazolide-free salts [(C6H6)CaN(SiMe3)2]2[B(C6F5)4]2 (1A) and [(C7H8)Ca{N(SiMe3)2}2][B(C6F5)4]2 (1B) were isolated, indicating the cleavage of the metal-nitrogen bond to the carbazolyl moiety. With the THF-free starting material, a methyl group from a trimethylsilyl moiety was abstracted instead. Subsequently, the generated silylium ion inserted into the metal-nitrogen bond between the carbazolyl ligand and the calcium metal, yielding [dtbpCbz-SiMe2-N(SiMe3)-Ca][B(C6F5)4] (2) as the product.
More Related Videos
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
10:44Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Related Concept Videos
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Acid Halides to Amides: Aminolysis
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Amides to Carboxylic Acids: Hydrolysis
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...