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In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
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Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
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In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
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Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...
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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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Updated: Jul 4, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Recent advances in oxidative chlorination.

Hai-Lei Cui1

  • 1Laboratory of Asymmetric Synthesis, College of Chemistry and Environmental Engineering, Chongqing University of Arts and Sciences, 319 Honghe Ave., Yongchuan, Chongqing, 402160, PR China. cuihailei616@163.com.

Organic & Biomolecular Chemistry
|February 5, 2024
PubMed
Summary
This summary is machine-generated.

Developing green oxidative chlorination methods is crucial for organic chlorides. This review covers practical, in situ generated chlorinating species from accessible chlorides and oxidants from 2013-2023.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Organic chlorides are widely used in various research fields.
  • There is a significant need for efficient, practical, and environmentally friendly chlorination techniques.

Purpose of the Study:

  • To review recent advancements in oxidative chlorination methodologies.
  • To highlight methods utilizing readily available chlorides and oxidants for in situ generation of active chlorinating species.

Main Methods:

  • Focuses on oxidative chlorination strategies.
  • Utilizes accessible chlorides (e.g., NaCl, HCl, KCl, CHCl3) and various oxidants.
  • Summarizes methodologies developed between 2013 and 2023.

Main Results:

  • Oxidative chlorination offers advantages like using inexpensive and safe starting materials.
  • This approach ensures good atom economy for chlorine.
  • A variety of oxidants can be employed, providing flexibility.

Conclusions:

  • Oxidative chlorination is an attractive strategy for synthesizing organic chlorides.
  • The review provides a comprehensive overview of recent developments in this field.
  • These methods are practical, cost-effective, and align with green chemistry principles.