Related Experiment Video
Updated: Mar 29, 2026
10:44
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
11.9K
Base catalysed decomposition of anthracene endoperoxide.
M Klaper1, P Wessig1, T Linker1
1Department of Chemistry, University of Potsdam, Karl-Liebknecht-Str. 24-25, 14476 Potsdam, Germany. linker@uni-potsdam.de.
Chemical Communications (Cambridge, England)
|November 27, 2015
Summary
Weak bases catalyze anthracene endoperoxide decomposition to anthraquinone. This reaction conveniently generates hydrogen peroxide under mild conditions, offering a new synthetic route.
Area of Science:
- Organic Chemistry
- Reaction Mechanisms
Background:
- Anthracene endoperoxides are intermediates in photochemical reactions.
- Their decomposition typically requires specific conditions.
Purpose of the Study:
- To investigate the catalytic decomposition of anthracene endoperoxides.
- To elucidate the reaction mechanism.
- To explore a convenient method for hydrogen peroxide generation.
Main Methods:
- Isolation of reaction intermediates.
- Density Functional Theory (DFT) calculations.
- Catalysis using weak bases.
Main Results:
- Catalytic amounts of weak bases efficiently decompose anthracene endoperoxides to anthraquinone.
- Key intermediates were isolated and characterized.
- DFT calculations supported the proposed reaction pathway.
Conclusions:
- A novel, mild, and convenient method for generating hydrogen peroxide has been developed.
- The mechanism involves base-catalyzed decomposition of anthracene endoperoxides.
- This pathway offers a practical approach for synthesizing anthraquinone and hydrogen peroxide.
More Related Videos
Related Concept Videos
02:26Base-Catalyzed Ring-Opening of Epoxides
11.1K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
11.1K
03:00Preparation of Epoxides
9.8K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
9.8K
00:51Radical Formation: Elimination
2.4K
Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect...
2.4K
01:22Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
5.3K
Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is activated by...
The carbonyl center is activated by...
5.3K
01:18Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
2.8K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.8K
02:04Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
8.1K
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.
8.1K