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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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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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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

5.8K
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.
5.8K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

8.6K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
8.6K
Oxidation of Alcohols02:37

Oxidation of Alcohols

13.1K
In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
13.1K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.3K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.3K
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

3.4K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
3.4K

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Light-driven Enzymatic Decarboxylation
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Selective Oxidation Using In Situ-Generated Hydrogen Peroxide.

Richard J Lewis1, Graham J Hutchings1

  • 1Max Planck-Cardiff Centre on the Fundamentals of Heterogeneous Catalysis FUNCAT, Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Cardiff, CF24 4HQ, United Kingdom.

Accounts of Chemical Research
|December 20, 2023
PubMed
Summary
This summary is machine-generated.

This study introduces in situ hydrogen peroxide (H₂O₂) generation, offering a sustainable alternative to industrial H₂O₂ production. This approach enhances chemical synthesis efficiency and reduces environmental impact.

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Hydrogen Production and Utilization in a Membrane Reactor
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Area of Science:

  • Green Chemistry and Sustainable Chemical Synthesis
  • Catalysis (Heterogeneous and Enzymatic)
  • Oxidative Transformations

Background:

  • Current industrial hydrogen peroxide (H₂O₂) production is energy-intensive, relies on quinone carriers with efficiency limitations, and involves separation challenges.
  • There is a growing need for sustainable chemical manufacturing processes with reduced greenhouse gas emissions and improved atom efficiency.
  • Direct synthesis and in situ utilization of H₂O₂ offer a promising route to overcome the drawbacks of conventional H₂O₂ production.

Purpose of the Study:

  • To develop and demonstrate an efficient in situ generation and utilization strategy for hydrogen peroxide (H₂O₂) in chemical synthesis.
  • To explore the potential of in situ H₂O₂ generation for feedstock valorization, particularly in propylene epoxidation.
  • To establish a chemo-enzymatic one-pot approach for bulk and fine chemical synthesis using in situ generated H₂O₂.

Main Methods:

  • Development of highly active catalysts for the direct synthesis of H₂O₂ from H₂ and O₂ with >99% H₂ utilization.
  • Implementation of in situ H₂O₂ generation coupled with subsequent utilization in oxidative transformations, including chemo-catalytic and enzymatic reactions.
  • Application of a chemo-catalytic/enzymatic one-pot strategy utilizing peroxygenase enzymes for C-H bond functionalization.

Main Results:

  • Demonstrated in situ H₂O₂ synthesis that rivals state-of-the-art industrial processes for oxidative transformations.
  • Achieved high rates of conversion and selectivity in propylene epoxidation using in situ generated H₂O₂, overcoming limitations of previous methods.
  • Successfully employed a chemo-enzymatic approach for C-H functionalization, inhibiting non-enzymatic pathways and operating at near-ambient conditions.

Conclusions:

  • In situ H₂O₂ synthesis represents a significant advancement for process intensification and decarbonization in the chemical industry.
  • The chemo-enzymatic one-pot approach offers a cost-effective and selective method for chemical synthesis and environmental remediation.
  • This technology holds substantial promise for unlocking new chemistries and improving the sustainability of chemical manufacturing.