Related Experiment Video
Updated: May 26, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Structural influence of steric factors and donor functions on lithium silylamides in non-coordinating solvents
Victoria P Colquhoun1, Carsten Strohmann
1Anorganische Chemie, Technische Universität Dortmund, 44227, Dortmund, Germany.
Abstract:
We herein present the synthesis and crystallographic characterisation of lithium silylamides displaying different coordination numbers and aggregation states according to the number of N- and O-donor functions in the starting material, (aminomethyl) substituted silazane ligands. The dimeric dimethyl-(N-lithio-tert-butylamino)-piperidinomethyl)-silane and dimethyl-(N-lithio-iso-propylamino)-piperidinomethyl)-silane, with three-coordinate lithium centres, were prepared by deprotonation of the corresponding silazane with (n)BuLi. Using the tridentate silazane (1R,2R)-N(1)-[{(tert-butylamino)-dimethylsilyl}methyl]-N(1),N(2),N(2)-trimethylcyclohexane-1,2-diamine a mixed "dimer" of lithium silylamide and lithium silanolate with four-coordinate lithium centres was obtained. Additionally, a monomeric lithium silylamide was synthesised using the tridentate [bis(methoxyethyl)aminomethyl] side arm.
More Related Videos
06:561,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
Published on: October 10, 2016
09:45Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
Published on: March 20, 2017
Related Concept Videos
Solvating Effects
Metal-Ligand Bonds
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
α-Alkylation of Ketones via Enolate Ions
Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction
Radical Reactivity: Steric Effects
Along with electronic factors, steric factors also account...
Acid Halides to Alcohols: LiAlH4 Reduction
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...