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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.

Preparation of Epoxides

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

Oxidative Cleavage of Alkenes: Ozonolysis

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

Oxymercuration-Reduction of Alkenes

Oxymercuration-Reduction of Alkenes

Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions generating free carboxylic acid...

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Updated: May 12, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Spontaneous and Efficient Oxime Synthesis by Al-Catalyst Assembly.

Shu-Lin Meng^1,2, Wen-Jie Kang^1,2, Chen-Ho Tung^1,2

¹Key Laboratory of Supramolecular Photochemistry & CAS-HKU Joint Laboratory on New Materials, New Cornerstone Science Laboratory, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, P. R. China.

Journal of the American Chemical Society

|May 11, 2026

Summary

Researchers developed a spontaneous oxime synthesis method under ambient conditions. This energy-efficient process utilizes aluminum and a catalyst with nitrogen oxides (NOx) for high-yield production of valuable nitrogenous compounds.

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Area of Science:

Organic Chemistry
Green Chemistry
Materials Science

Background:

Oxime synthesis traditionally demands significant energy input for multielectron transformations.
Nitrogenous compounds, including oximes, are crucial in various chemical applications.

Purpose of the Study:

To develop a novel, energy-efficient method for oxime synthesis under ambient conditions.
To explore the use of aluminum and NOx reduction catalysts in spontaneous C-N coupling reactions.

Main Methods:

Assembling aluminum (Al) with a NOx (x=2, 3) reduction catalyst.
Utilizing CuZn alloy foil as a stable and efficient catalyst.
Integrating plasma-driven N2 oxidation for tandem synthesis.
Employing abundant NOx feedstocks and recycled Al resources.

Main Results:

Achieved spontaneous oxime synthesis with excellent yields under ambient conditions.
Demonstrated high capacity for electron transfer using aluminum.
Showcased extraordinary catalytic stability with CuZn alloy foil.
Enabled gram-scale, air-to-oxime synthesis from NOx feedstocks.
Confirmed broad substrate scope, including bioactive molecules and drug precursors.

Conclusions:

The developed method offers a profitable and energy-efficient route for oxime synthesis.
This approach provides convenient access to value-added nitrogenous compounds from abundant resources.
The process is suitable for synthesizing complex molecules, including pharmaceuticals.