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Updated: Jun 25, 2025

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Published on: February 6, 2019

Electrocatalytic ORR-coupled ammoximation for efficient oxime synthesis.

Yujia Yuan¹, Lisong Chen^1,2, Zhipeng Wan¹

¹State Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.

Science Advances

|May 24, 2024

Summary

This study introduces an electrochemistry-assisted method for producing cyclohexanone oxime under ambient conditions. This green chemistry approach utilizes in situ generated reactive oxygen species (ROS) for efficient and sustainable oxime synthesis.

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Published on: June 20, 2014

Area of Science:

Green Chemistry
Electrocatalysis
Organic Synthesis

Background:

Conventional cyclohexanone oxime production requires harsh conditions (high temperature/pressure) and expensive reagents.
Existing methods often involve hazardous hydroxylamine sulfate or oxidants, posing environmental and economic challenges.

Purpose of the Study:

To develop a mild, economical, and sustainable electrocatalytic route for cyclohexanone oxime production.
To utilize in situ generated green oxidants for efficient ammoximation under ambient conditions.

Main Methods:

An electrochemistry-assisted cascade strategy was employed using a cathode for in situ generation of reactive oxygen species (ROS).
The reaction utilized oxygen, ammonium bicarbonate, and cyclohexanone as reactants.
Mechanistic studies involved analyzing the role of Ti-MOR in capturing OOH* and converting H2O2.

Main Results:

Achieved over 95% yield and 99% selectivity for cyclohexanone oxime.
Demonstrated a high electron-to-oxime (ETO) efficiency of 96%.
Identified ROS (OOH* and H2O2) as key intermediates in the electrocatalytic process.

Conclusions:

The proposed electrochemical route offers a sustainable and energy-efficient alternative for oxime production.
In situ generation of ROS at the cathode enables efficient cyclohexanone ammoximation under mild conditions.
Ti-MOR plays a crucial role in accelerating the cascade reaction, enhancing overall efficiency.