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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

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Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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Updated: Jun 13, 2025

Improved Heterojunction Quality in Cu2O-based Solar Cells Through the Optimization of Atmospheric Pressure Spatial Atomic Layer Deposited Zn1-xMgxO

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Solvent-mediated oxide hydrogenation in layered cathodes.

Gang Wan^1,2, Travis P Pollard³, Lin Ma^3,4

¹SLAC National Accelerator Laboratory, Menlo Park, CA 94025, USA.

Science (New York, N.Y.)

|September 12, 2024

Summary

This summary is machine-generated.

Hydrogenation, not just lithium diffusion, causes self-discharge in lithium-ion battery cathodes. This process creates gradients that accelerate battery degradation and reduce lifespan.

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Area of Science:

Materials Science
Electrochemistry
Energy Storage

Background:

Self-discharge and mechanical degradation limit the lifespan of energy storage devices.
In lithium-ion batteries, cathode self-discharge leads to capacity and voltage loss.
Current models primarily attribute self-discharge to lithium-ion diffusion into the cathode.

Purpose of the Study:

To investigate an alternative mechanism for self-discharge in layered transition metal oxide cathodes.
To understand the role of hydrogenation in battery degradation.
To explore the impact of hydrogenation on cathode chemo-mechanical coupling and calendar life.

Main Methods:

Analysis of self-discharged cathodes.
Investigation of hydrogen transfer from carbonate solvents to delithiated oxides.
Observation of proton and lithium ion concentration gradients.

Main Results:

Demonstrated hydrogenation as an alternative pathway for cathode self-discharge.
Identified hydrogen transfer from carbonate solvents to delithiated oxides.
Observed opposing proton and lithium ion gradients in self-discharged cathodes, leading to heterogeneity and accelerated degradation.

Conclusions:

Hydrogenation of delithiated cathodes is a significant self-discharge pathway.
This process contributes to chemical and structural heterogeneities, impacting battery performance.
Hydrogenation affects chemo-mechanical coupling and calendar life in lithium-ion batteries.