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Hydrolysis of Chlorobenzene to Phenol: Dow Process

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

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.

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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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.

Photochemical Electrocyclic Reactions: Stereochemistry

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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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.

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Related Experiment Video

Updated: Jul 12, 2026

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

[(DPEPhos)(bcp)Cu]PF₆: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

When Dowd-Beckwith reaction meets photocatalysis.

Zhichao Zhang¹, Lipeng Qiao^1,2, Kai Sun¹

¹College of Chemistry, Zhengzhou University, Zhengzhou 450001, China. bingyu@zzu.edu.cn.

Organic & Biomolecular Chemistry

|July 10, 2026

Summary

Photocatalysis has revolutionized the Dowd-Beckwith reaction, enabling efficient synthesis of medium-sized carbocycles. This review explores recent advances in photocatalytic ring-expansion methods, offering new insights for carbocycle synthesis.

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Last Updated: Jul 12, 2026

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Synthesis and Performance Evaluations of ZnCoS/ZnCdS with Twin Crystal Structure for Multifunctional Redox Photocatalysis in Energy Applications

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Published on: July 25, 2025

Area of Science:

Organic Chemistry
Synthetic Chemistry
Photocatalysis

Background:

The Dowd-Beckwith reaction is a key method for creating medium-sized carbocyclic frameworks.
Classical Dowd-Beckwith protocols have inherent limitations.
Photocatalysis offers a novel approach to overcome these limitations.

Purpose of the Study:

To review recent advancements in photocatalytic Dowd-Beckwith ring-expansion reactions.
To categorize methodologies based on radical initiation.
To discuss mechanistic features of these reactions.

Main Methods:

Literature review of photocatalytic Dowd-Beckwith reactions.
Categorization of methods by radical initiation mode.
Analysis of reaction mechanisms.

Main Results:

Photocatalysis provides a distinct platform for Dowd-Beckwith reactions.
Recent advances have expanded the scope and efficiency of these reactions.
Different radical initiation modes offer diverse synthetic pathways.

Conclusions:

Photocatalytic Dowd-Beckwith reactions represent a significant advancement in carbocycle synthesis.
This approach circumvents limitations of traditional methods.
The review provides insights for the practical synthesis of medium-sized carbocycles.