Related Experiment Video
Updated: Mar 14, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Synthesis and Reactivity of Discrete Calcium Imides
Benjamin M Wolf1, Cäcilia Maichle-Mössmer1, Reiner Anwander2
1Institut für Anorganische Chemie, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, 72076, Tübingen, Germany.
Abstract:
Protonolysis of dibenzylcalcium with triphenylsilylamine affords a thf-coordinated tetrametallic calcium imide with a heterocuboid core structure. The use of calcium bis(tetramethylaluminate) as a precursor for tandem salt metathesis/protonolysis reactions with alkali metal amides of 2,6-diisopropylaniline and triphenylsilylamine provides access to Lewis acid stabilized monocalcium imides of the type [(thf)4 Ca(μ2 -NR)(μ2 -Me)AlMe2 ]. Treatment of [(thf)4 Ca(μ2 -NSiPh3 )(μ2 -Me)AlMe2 ] with phenylsilane results in H-Si addition across the Ca-N imido bond, producing a homoleptic calcium amidoaluminate complex and putative CaH2 whereas reaction with phenylacetylene leads to protonation of an AlMe moiety to yield the dimeric complex [(thf)Ca{NSiPh3 }{AlMe2 (CCPh)}]2 .
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...
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Amides to Amines: LiAlH4 Reduction
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
Preparation of Acid Anhydrides
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...

