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Preparation of Epoxides03:00

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 peroxy acids to...
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
Acid-Catalyzed Ring-Opening of Epoxides02:24

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...
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
Sharpless Epoxidation02:57

Sharpless Epoxidation

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...
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...

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A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
09:08

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes

Published on: February 27, 2017

Enantioselective epoxide polymerization using a bimetallic cobalt catalyst.

Renee M Thomas1, Peter C B Widger, Syud M Ahmed

  • 1Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, United States.

Journal of the American Chemical Society
|November 4, 2010
PubMed
Summary
This summary is machine-generated.

A novel cobalt catalyst enables rapid, highly stereoselective polymerization of epoxides, yielding isotactic polyethers. This breakthrough offers a new method for synthesizing polymers with excellent thermal properties.

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Area of Science:

  • Polymer Chemistry
  • Organometallic Chemistry

Background:

  • Enantioselective polymerization is crucial for creating stereoregular polymers.
  • Developing efficient catalysts for stereoselective epoxide polymerization remains a challenge.

Purpose of the Study:

  • To explore a highly active enantiopure bimetallic cobalt complex for enantioselective epoxide polymerization.
  • To optimize polymerization conditions for high rates and stereoselectivity.
  • To investigate the synthesis of isotactic polyethers from racemic epoxides.

Main Methods:

  • Utilized a highly active enantiopure bimetallic cobalt complex.
  • Performed enantioselective polymerization of various monosubstituted epoxides.
  • Optimized reaction conditions to achieve high stereoselectivity (s-factors > 50, some > 300).
  • Employed a racemic catalyst to prepare isotactic polyethers.

Main Results:

  • Achieved high polymerization rates and stereoselectivity for a range of epoxides.
  • Produced polymers with high isotacticity (mm triads > 95%, some > 98%).
  • Synthesized isotactic polyethers in quantitative yields using a racemic catalyst.
  • Demonstrated high melting temperatures (T(m)) for the resulting isotactic polyethers.

Conclusions:

  • The bimetallic cobalt complex is highly effective for rapid enantioselective polymerization of epoxides.
  • This work presents the first report of rapid synthesis of diverse, highly isotactic polyethers from racemic epoxides.
  • The developed method provides a valuable route to stereoregular polyethers with desirable thermal properties.