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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.9K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
2.9K
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

11.3K
In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday...
11.3K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
2.9K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.2K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
4.2K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.3K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.3K
Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

Autoxidation of Ethers to Peroxides and Hydroperoxides

8.1K
Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
8.1K

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Related Experiment Video

Updated: Sep 4, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Aromatic Endoperoxides.

Edward L Clennan1

  • 1Department of Chemistry, University of Wyoming, Laramie, WY.

Photochemistry and Photobiology
|July 15, 2022
PubMed
Summary

Aromatic endoperoxides are reviewed for their synthesis and reactions. Understanding factors influencing their formation and singlet oxygen release is key for applications in electronics and preventing hydrocarbon degradation.

Area of Science:

  • Organic Chemistry
  • Materials Science

Background:

  • Aromatic hydrocarbons serve dual roles as endoperoxide precursors and components in electronic/photonic devices.
  • Controlling endoperoxide formation is vital for both synthesizing these compounds and preventing degradation of aromatic materials.

Purpose of the Study:

  • To review fundamental aspects of aromatic endoperoxide chemistry, focusing on synthesis and reactions.
  • To discuss factors influencing endoperoxide formation and structural control over singlet oxygen release.
  • To highlight the need for improved synthesis methods and prevention strategies for aromatic endoperoxides.

Main Methods:

  • Review of existing literature on aromatic endoperoxide synthesis.
  • Analysis of factors affecting endoperoxide formation and stability.

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Last Updated: Sep 4, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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  • Examination of structural features related to singlet oxygen release.

    • Main Results:

    • Aromatic endoperoxides have diverse applications, necessitating improved synthesis.
    • Factors enhancing/preventing endoperoxide formation are identified.
    • Structural modifications can control singlet oxygen release capabilities.

    Conclusions:

    • Enhanced synthesis methods are crucial for new applications of aromatic endoperoxides.
    • Preventing endoperoxide formation is essential for preserving aromatic hydrocarbons in semiconductor applications.
    • Further research into aromatic endoperoxide chemistry will benefit both synthetic applications and material stability.