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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.

Oxidative Cleavage of Alkenes: Ozonolysis

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 Alkenes

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 Osmium Tetraoxide

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.

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

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...

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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Related Experiment Video

Updated: May 23, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Peroxygenase-catalysed oxyfunctionalisation reactions.

Thomas Hilberath¹, Frank Hollmann¹, Florian Tieves²

¹Department of Biotechnology, Delft University of Technology, van der Maasweg 9, Delft, Netherlands.

Methods in Enzymology

|April 27, 2025

Summary

This summary is machine-generated.

Peroxygenases are heme-thiolate enzymes that efficiently hydroxylate C-H bonds using hydrogen peroxide. They offer a greener alternative to cytochrome P450s for biocatalysis.

Keywords:

Biocatalysis Green chemistry Hydrogen peroxide Oxyfunctionalisation Peroxygenases

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Area of Science:

Biocatalysis
Green Chemistry
Enzyme Engineering

Background:

Peroxygenases are heme-thiolate enzymes catalyzing selective oxyfunctionalization, including C-H hydroxylation.
They offer advantages over cytochrome P450s by directly using hydrogen peroxide (H2O2), simplifying cofactor requirements.
Key enzymes include chloroperoxidase and unspecific peroxygenases from Agrocybe aegerita.

Purpose of the Study:

To review the mechanistic pathways of peroxygenase-catalyzed reactions.
To examine strategies for enhancing peroxygenase applications in green chemistry.
To discuss challenges and advancements in scalability and operational stability.

Main Methods:

Exploration of peroxygenase mechanistic pathways, focusing on Compound I formation and decay.
Examination of in situ H2O2 generation and substrate loading strategies.
Review of enzyme and reaction engineering for improved selectivity and stability.

Main Results:

Peroxygenases demonstrate high selectivity in oxyfunctionalization reactions, particularly C-H bond hydroxylation.
Direct utilization of H2O2 circumvents limitations associated with traditional P450 systems.
Enzyme and reaction engineering offer routes to enhance regio- and stereoselectivity.

Conclusions:

Peroxygenases are promising biocatalysts for sustainable oxyfunctionalization, offering a green alternative to conventional synthesis.
Addressing challenges in scalability and stability through immobilization and non-aqueous media is crucial for industrial adoption.
Continued research in enzyme engineering will further unlock the potential of peroxygenases.