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Preparation of Epoxides03:00

Preparation of Epoxides

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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 peroxy...
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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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Acid-Catalyzed Ring-Opening of Epoxides02:24

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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...
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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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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Preparation of Highly Porous Coordination Polymer Coatings on Macroporous Polymer Monoliths for Enhanced Enrichment of Phosphopeptides
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Metalloporphyrinic framework containing multiple pores for highly efficient and selective epoxidation.

Xiu-Li Yang1, Chuan-De Wu

  • 1Center for Chemistry of High-Performance and Novel Materials, Department of Chemistry, Zhejiang University , Hangzhou 310027, P. R. China.

Inorganic Chemistry
|May 3, 2014
PubMed
Summary

This study details a novel porous porphyrinic framework constructed from metalloporphyrin and zinc carboxylate units. This framework efficiently catalyzes olefin epoxidation with remarkable substrate size selectivity.

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Area of Science:

  • Materials Science
  • Catalysis
  • Coordination Chemistry

Background:

  • Porous materials are crucial for catalysis.
  • Metalloporphyrins offer versatile catalytic properties.
  • Developing stable and selective catalytic frameworks is an ongoing challenge.

Purpose of the Study:

  • To synthesize a novel porous porphyrinic framework.
  • To investigate its catalytic activity in olefin epoxidation.
  • To evaluate the framework's efficiency, stability, and selectivity.

Main Methods:

  • Construction of a porous framework using metalloporphyrin Mn(III)Cl-5,10,15,20-tetrakis(3,5-biscarboxylphenyl)porphyrin and paddle-wheel Zn2(COO)4 units.
  • Characterization of the framework's structure and porosity.
  • Testing the framework's performance in olefin epoxidation reactions.

Main Results:

  • Successful synthesis of a stable porous porphyrinic framework.
  • Demonstrated high efficiency in catalyzing olefin epoxidation.
  • Exhibited excellent substrate size selectivity, distinguishing between different olefin sizes.

Conclusions:

  • The constructed porous porphyrinic framework is a highly efficient and stable catalyst for olefin epoxidation.
  • The framework's design enables precise control over substrate selectivity.
  • This work presents a promising new material for selective catalytic transformations.