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Related Concept Videos

Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

Autoxidation of Ethers to Peroxides and Hydroperoxides

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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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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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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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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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Sharpless Epoxidation02:57

Sharpless Epoxidation

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The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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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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Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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Highly Efficient Autoxidation of Triethylamine.

Eva R Kjærgaard1, Kristian H Møller1, Torsten Berndt2

  • 1Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark.

The Journal of Physical Chemistry. A
|October 6, 2023
PubMed
Summary
This summary is machine-generated.

Triethylamine (TEA) undergoes rapid atmospheric autoxidation, forming highly oxygenated products. This process, faster than in other amines, involves efficient H-shift reactions and is confirmed by experimental observations.

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Area of Science:

  • Atmospheric Chemistry
  • Organic Chemistry
  • Chemical Kinetics

Background:

  • Autoxidation is a key oxidation pathway for atmospheric compounds like isoprene and terpenes.
  • It has also been identified as dominant in the oxidation of dimethyl sulfide (DMS) and trimethylamine (TMA).

Purpose of the Study:

  • To investigate the autoxidation mechanism of triethylamine (TEA) in the atmosphere.
  • To determine the rate of unimolecular reactions and H-shift processes following OH + TEA.
  • To identify and verify the formation of highly oxygenated products.

Main Methods:

  • Theoretical multiconformer transition-state theory (MC-TST) calculations.
  • Flow-tube experiments to observe reaction products and radicals.

Main Results:

  • Triethylamine (TEA) exhibits exceptionally fast atmospheric autoxidation, exceeding rates observed for DMS and TMA.
  • Products with up to three hydroperoxy (OOH) groups and an O:C ratio >1 are formed.
  • Rate coefficients for the first two generations of H-shifts exceed 20 s-1.
  • OH hydrogen abstraction is strongly favored at the α-carbon.

Conclusions:

  • Autoxidation is a dominant atmospheric oxidation pathway for TEA, leading to highly functionalized compounds.
  • Experimental results verify the theoretical predictions and the formation of proposed oxidized products and radicals.
  • The study highlights the significant role of TEA autoxidation in atmospheric chemistry.