Related Experiment Video
Updated: May 25, 2026

Preparation of Functional Silica Using a Bioinspired Method
Published on: August 1, 2018
Preparation of aminomethyl functionalised silanes via an α-lithiated amine: from their synthesis, stability and
Viktoria H Gessner1, Carsten Strohmann
1Anorganische Chemie, Technische Universität Dortmund, Otto-Hahn-Straße 6, 44263 Dortmund, Germany.
Abstract:
The preparation of aminomethyl functionalised silanes based on the α-lithiated amine, (1R,2R)-N,N,N',N'-tetramethylcyclohexane-1,2-diamine [(R,R)-TMCDA] is reported. This methodology can be applied for the synthesis of mono-aminomethyl substituted systems, but most remarkably also for di- and trifunctionalised compounds. The trapping of the lithiated amine is accompanied by transmetallation reactions resulting in the formation of (silylmethyl)silanes depending on the reaction temperature. The zinc(II) halide complexes of the mono-functionalised systems show the formation of exclusively one configuration of the stereogenic nitrogen atom, in which the spatially more demanding substituent exhibits the pseudo-equatorial position. The di- and trifunctionalised systems feature high sensitivity towards Si-C bond cleavage under re-formation of the (R,R)-TMCDA fragment.
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of Amines: Alkylation of Ammonia and Amines
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
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...
Preparation of Amines: Reduction of Amides and Nitriles
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
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...

