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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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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Oxidation of Alcohols02:37

Oxidation of Alcohols

12.7K
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:
12.7K
Radical Autoxidation01:20

Radical Autoxidation

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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

7.0K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
7.0K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

9.7K
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.
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Updated: May 21, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Thioether Oxidation Chemistry in Reactive Oxygen Species (ROS)-Sensitive Trigger Design: A Kinetic Analysis.

Ayatullah Gamal Abdelfattah1, Shubham Bansal1, Joanna Afokai Quaye1

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This summary is machine-generated.

Hydrogen peroxide (H2O2) slowly oxidizes thioethers, making it unlikely to trigger drug delivery. Hypochlorite, however, rapidly oxidizes thioethers, suggesting it is a more effective trigger for these systems.

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Area of Science:

  • Chemical kinetics
  • Oxidation reactions
  • Drug delivery systems

Background:

  • Thioether oxidation to sulfoxide is a known reactive oxygen species (ROS)-sensitive trigger for drug delivery.
  • Hydrogen peroxide (H2O2) is commonly cited as the ROS responsible for this activation.

Purpose of the Study:

  • To investigate the kinetics of thioether oxidation by H2O2 and hypochlorite under near-physiological conditions.
  • To determine the relative importance of H2O2 and hypochlorite in activating thioether-based drug delivery systems.

Main Methods:

  • Kinetic experiments were performed using a series of aryl thioethers.
  • Reaction rates and half-lives were measured at pathophysiologically relevant concentrations of H2O2 and hypochlorite.

Main Results:

  • H2O2 oxidation of thioethers exhibits half-lives of hundreds of hours under near-physiological conditions.
  • Hypochlorite oxidizes thioethers significantly faster, with half-lives ranging from seconds to minutes.
  • Sulfoxide formation by H2O2 is slow, while sulfone formation is even slower.

Conclusions:

  • Hypochlorite is a much more potent activator of thioether-based drug delivery systems than H2O2.
  • The slow oxidation rate of thioethers by H2O2 suggests limited utility in ROS-sensitive drug delivery.
  • Future drug delivery designs should consider hypochlorite as a primary ROS trigger.