Related Experiment Video
Updated: Jul 10, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Protection of lithium metal surfaces using chlorosilanes
Filippo Marchioni1, Kurt Star, Erik Menke
1Department of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, California 90095-1569, USA.
Abstract:
In this paper, we present a new approach for protecting metallic lithium surfaces based on a reaction between the thin native layer of lithium hydroxide present on the surface and various chlorosilane derivatives. The chemical composition of the resulting layer and the chemistry involved in layer formation were analyzed by polarization modulated infrared reflection absorption spectroscopy (PM-IRRAS), X-ray photoelectron spectroscopy (XPS), and energy dispersive X-ray analysis (EDX). Spectroscopy shows the disappearance of surface hydroxide groups and the appearance of silicon and chloride on the lithium surface. Differential scanning calorimetry (DSC) and electrochemical impedance spectroscopy (EIS) show that this surface treatment protects the lithium from certain gas-phase reactions and is ionically conductive.
Related Concept Videos
Preparation and Reactions of Sulfides
Preparation and Reactions of Thiols
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...

