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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.1K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.7K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
3.7K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

13.3K
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.
13.3K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.7K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.7K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.2K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
3.2K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.8K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.8K

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Inter-Atomic Synergy on Single-Atom Alloy Promotes Cyclohexanone Oxime Electrosynthesis.

Panlong Zhai1, Chen Wang2, Guan Sheng3

  • 1Department of Chemistry, City University of Hong Kong, Kowloon, Hong Kong SAR, P. R. China.

Advanced Materials (Deerfield Beach, Fla.)
|March 17, 2026
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Summary

This study introduces a novel Fe-Bi single-atom alloy catalyst for the efficient electrosynthesis of cyclohexanone oxime using renewable electricity. This sustainable method overcomes challenges in traditional industrial processes.

Keywords:
atomic‐scale synergistic mechanismcyclohexanone oximeelectrocatalytic C─N coupling reactionsingle‐atom alloy

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Area of Science:

  • Electrochemistry
  • Materials Science
  • Catalysis

Background:

  • Traditional synthesis of cyclohexanone oxime is energy-intensive and hazardous.
  • Existing electrosynthesis methods face challenges with intermediate over-reduction and inefficient C─N coupling.

Purpose of the Study:

  • To develop a sustainable and efficient electrosynthesis route for cyclohexanone oxime.
  • To investigate a novel single-atom alloy catalyst for improved activity and selectivity.

Main Methods:

  • Electrosynthesis using a Fe1Bi single-atom alloy (SAA) catalyst.
  • In situ electrochemical spectroscopic measurements.
  • Density functional theory (DFT) calculations.
  • Techno-economic analysis using flow electrolyzer data.

Main Results:

  • The Fe1Bi SAA catalyst achieved 70.9% Faradaic efficiency and a yield rate of 0.94 mmol cm⁻² h⁻¹ for cyclohexanone oxime.
  • Identified a synergistic mechanism involving Fe activating cyclohexanone and Bi reducing nitrite to hydroxylamine.
  • Demonstrated the potential economic viability of the process.

Conclusions:

  • The Fe-Bi atomic interfaces in the SAA catalyst enable cooperative catalysis for efficient C─N coupling.
  • This work offers atomic-level insights into electrosynthesis of organonitrogen compounds.
  • The developed method presents a sustainable alternative to conventional industrial processes.