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Related Concept Videos

Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

Autoxidation of Ethers to Peroxides and Hydroperoxides

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.

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Related Experiment Video

Updated: Jul 19, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
06:18

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

Singlet oxygen generation from lophine hydroperoxides.

M Kimura1, G H Lu, H Nishigawa

  • 1Department of Chemistry, Faculty of Science, Okayama University, 700-8530 Okayama, Japan. kimuram@cc.okayama-u.ac.jp

Luminescence : the Journal of Biological and Chemical Luminescence
|November 8, 2006
PubMed
Summary

Singlet oxygen generation from lophine hydroperoxides is influenced by substituent groups. Electron-withdrawing groups promote singlet oxygen formation, while electron-donating groups enhance chemiluminescence.

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Light-driven Enzymatic Decarboxylation
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Light-driven Enzymatic Decarboxylation

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Last Updated: Jul 19, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
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Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

Area of Science:

  • Organic Chemistry
  • Photochemistry

Background:

  • Lophine hydroperoxides are known chemiluminescent compounds.
  • Singlet oxygen is a reactive oxygen species with significant chemical and biological implications.

Purpose of the Study:

  • To investigate the substituent effects on singlet oxygen formation from lophine hydroperoxides.
  • To correlate electronic properties of substituents with the efficiency of singlet oxygen generation and chemiluminescence.

Main Methods:

  • Synthesis of 2-(p-substituted phenyl) lophine peroxides (2a-c).
  • Detection of singlet oxygen using 1,3-diphenyl-isobenzofuran as a trapping agent.
  • Quantification of singlet oxygen yield and chemiluminescence intensity.

Main Results:

  • Efficient formation of singlet oxygen (up to 80% with a nitro group) was observed with electron-withdrawing substituents.
  • Electron-donating groups were found to enhance the overall chemiluminescence efficiency.
  • A clear correlation between substituent electronic nature and reaction pathway was established.

Conclusions:

  • The electronic nature of substituents on lophine hydroperoxides plays a crucial role in directing the reaction pathway.
  • Electron-withdrawing groups favor singlet oxygen generation, while electron-donating groups enhance light emission.
  • This study provides insights into the mechanism of chemiluminescence and singlet oxygen production in substituted lophine systems.