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Related Concept Videos

Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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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.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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

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

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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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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 acids to...
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Sharpless Epoxidation02:57

Sharpless Epoxidation

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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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Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

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Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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Updated: Jan 19, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
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Cyclic Polyester Formation with an [OSSO]-Type Iron(III) Catalyst.

Salvatore Impemba1, Francesco Della Monica1, Alfonso Grassi1

  • 1Dipartimento di Chimica e Biologia "Adolfo Zambelli", Università degli Studi di Salerno, Via Giovanni Paolo II, 132-, 84084, Fisciano (SA), Italy.

Chemsuschem
|September 28, 2019
PubMed
Summary
This summary is machine-generated.

A novel iron catalyst efficiently forms cyclic polyesters from lactide, caprolactone, and butyrolactone via ring-opening polymerization. This robust catalyst demonstrates high activity and produces cyclic polymers with consistent ring sizes.

Keywords:
cyclizationhomogeneous catalysisironpolymersring-opening polymerization

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Area of Science:

  • Polymer Chemistry
  • Organometallic Chemistry
  • Materials Science

Background:

  • Ring-opening polymerization (ROP) is crucial for synthesizing polyesters.
  • Developing efficient catalysts for controlled polyester formation remains a key challenge.
  • Cyclic polyesters offer unique properties but their synthesis is often complex.

Purpose of the Study:

  • To investigate the efficacy of a novel iron-bis(phenolic) complex as a catalyst for polyester synthesis.
  • To explore the formation of cyclic polyesters from various lactone monomers.
  • To elucidate the polymerization mechanism and catalyst performance.

Main Methods:

  • Ring-opening polymerization of lactide, ϵ-caprolactone, and β-butyrolactone.
  • Catalysis using a 1,4-dithiabutanedyl-2,2'-bis(4,6-dicumylphenol) [OSSO]-FeCl complex activated with cyclohexene oxide.
  • Characterization of cyclic polymers using high-resolution matrix-assisted laser desorption ionization mass spectrometry (MALDI-MS).
  • Kinetic studies to propose a polymerization mechanism.

Main Results:

  • The [OSSO]-FeCl complex demonstrated high catalytic activity (turnover frequency up to 2718 h-1) for cyclic polyester formation.
  • The catalyst was robust, effective at high monomer/Fe ratios (up to 10,000), and produced polymers with consistent average ring sizes (e.g., ≈5 kDa for cyclic polylactide).
  • MALDI-MS confirmed the formation of cyclic polymer structures.

Conclusions:

  • The [OSSO]-FeCl complex is a highly efficient catalyst for the ROP of lactones to form cyclic polyesters.
  • A monometallic ring-opening polymerization/cyclization mechanism is proposed based on kinetic data.
  • This catalytic system offers a promising route for controlled synthesis of cyclic polyesters with tunable properties.