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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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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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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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Base-Catalyzed Ring-Opening of Epoxides02:26

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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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Anionic Chain-Growth Polymerization: Overview01:20

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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Cationic Chain-Growth Polymerization: Mechanism00:57

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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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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Reversible redox controlled acids for cationic ring-opening polymerization.

Michael J Supej1, Elizabeth A McLoughlin1, Jesse H Hsu1

  • 1Department of Chemistry and Chemical Biology, Cornell University Ithaca New York 14853 USA bpf46@cornell.edu.

Chemical Science
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Summary
This summary is machine-generated.

Ferrocene-derived catalysts offer new control over ring-opening polymerization (ROP) for creating advanced polymers. This breakthrough enables precise chemical and electrochemical tuning of polymerization, advancing material science applications.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Catalysis

Background:

  • Externally controlled polymerization is key for novel polymer structures and advanced technologies like lithography and 3D printing.
  • Externally controlled ring-opening polymerization (ROP) is particularly interesting for creating biocompatible and biodegradable block polymers.
  • Current photoacid generator-mediated ROPs suffer from catalyst instability and poor temporal control, limiting their applications.

Purpose of the Study:

  • To develop a new class of catalysts for externally controlled ring-opening polymerization (ROP).
  • To achieve precise chemical and electrochemical control over ROP using redox-switchable catalysts.
  • To overcome the limitations of stability and temporal control in existing ROP methodologies.

Main Methods:

  • Synthesis of ferrocene-derived acid catalysts.
  • Utilizing reversible oxidation and reduction of the ferrocenyl moiety to modulate catalyst acidity.
  • Applying these catalysts to control the ring-opening polymerization (ROP) of cyclic esters.

Main Results:

  • A novel class of ferrocene-derived acid catalysts was successfully synthesized.
  • The acidity of these catalysts can be reversibly tuned via redox stimuli.
  • The catalysts demonstrated effective control over the ring-opening polymerization (ROP) of cyclic esters.

Conclusions:

  • Ferrocene-derived catalysts offer a robust platform for externally controlled ROP.
  • Redox-switchable catalysis provides precise temporal and chemical control over polymer synthesis.
  • This approach advances the development of advanced polymeric materials for diverse applications.