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Preparation of Epoxides03:00

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Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
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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...
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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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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...
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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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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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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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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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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Chemoselective Polymerizations from Mixtures of Epoxide, Lactone, Anhydride, and Carbon Dioxide.

Charles Romain1, Yunqing Zhu1, Paul Dingwall1

  • 1Department of Chemistry, Imperial College London , London SW7 2AZ, U.K.

Journal of the American Chemical Society
|March 23, 2016
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Summary
This summary is machine-generated.

A novel dizinc catalyst enables precise control over polymer composition by switching between different polymerization types. This breakthrough allows for the creation of polymers with engineered block sequences and predictable ester and carbonate structures.

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Area of Science:

  • Polymer Chemistry
  • Catalysis
  • Materials Science

Background:

  • Controlling polymer composition from monomer mixtures is a significant challenge in polymer science.
  • Existing methods often lack the ability to precisely dictate sequence and composition.

Purpose of the Study:

  • To investigate a single switchable catalyst for both ring-opening polymerization (ROP) and ring-opening copolymerization (ROCOP).
  • To achieve control over polymer block sequences and predictable compositions using a single catalytic system.

Main Methods:

  • Utilized experimental and theoretical methods to study a dizinc catalyst.
  • Investigated the copolymerization of four model monomers: ε-caprolactone, cyclohexene oxide, phthalic anhydride, and carbon dioxide.
  • Analyzed monomer selectivity and catalyst switching behavior.

Main Results:

  • The dizinc catalyst demonstrated high selectivity for different monomers, enabling distinct polymerization cycles.
  • Achieved precise control over block sequence formation in polymers.
  • Successfully synthesized polymers with predictable ester and carbonate compositions.

Conclusions:

  • A single catalyst can effectively control orthogonal monomer reactivity for sequential polymerization.
  • Understanding metal-chain end group interactions is key to engineering polymer block sequences.
  • This approach offers a new pathway for designing complex polymer architectures with tailored properties.