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Oxidation and Reduction of Organic Molecules

Oxidation and Reduction of Organic Molecules

Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
The removal of an electron from a molecule, results in a...

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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.

Acid-Catalyzed Ring-Opening of Epoxides

Acid-Catalyzed Ring-Opening of Epoxides

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...

Oxidation of Phenols to Quinones

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...

Autoxidation of Ethers to Peroxides and Hydroperoxides

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.

Preparation of Epoxides

Preparation of Epoxides

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...

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Author Spotlight: Design and Evaluation of Au-Electroplated Carbon Fiber Cloth Electrodes for Hydrogen Peroxide Fuel Cells

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Epoxide Electroreduction.

Cheng Huang¹, Wan Ma¹, Xuelian Zheng¹

¹The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, P. R. China.

Journal of the American Chemical Society

|December 29, 2021

Summary

This summary is machine-generated.

This study introduces electrochemical epoxide hydrogenation, a novel method for synthesizing alcohols. It achieves selective Markovnikov or anti-Markovnikov ring opening without transition metals, offering a powerful new synthetic route.

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Area of Science:

Organic Chemistry
Electrochemistry
Catalysis

Background:

Selective hydrogenation of epoxides is a key transformation for alcohol synthesis.
Existing methods often require transition metal catalysts and struggle with regioselectivity.
Developing metal-free, selective epoxide functionalization remains a significant challenge.

Purpose of the Study:

To develop a novel electrochemical method for the selective hydrogenation of epoxides.
To achieve direct alcohol synthesis from epoxides using electrons and protons as reductants.
To explore both Markovnikov and anti-Markovnikov regioselectivity in epoxide ring opening.

Main Methods:

Electrochemical reduction of epoxides using electrons and protons.
Utilizing a wide range of primary, secondary, and tertiary epoxides.
Mechanistic studies involving in situ radical intermediates and kinetic analysis.

Main Results:

Successful synthesis of diverse primary, secondary, and tertiary alcohols.
Demonstration of selective Markovnikov and anti-Markovnikov epoxide ring opening.
Identification of factors controlling regioselectivity: thermodynamic stability of benzyl radicals (aryl epoxides) and kinetic control (alkyl epoxides).

Conclusions:

Electrochemical epoxide hydrogenation provides a versatile and metal-free pathway to alcohols.
Regioselectivity can be precisely controlled based on substrate type and reaction mechanisms.
This approach offers a sustainable and efficient alternative for alcohol synthesis.