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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.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
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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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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...
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Preparation and Reactions of Sulfides02:26

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Crystalline phosphino-functionalized mesoionic olefins (p-MIOs).

Arne Merschel1, Yury V Vishnevskiy1, Beate Neumann1

  • 1Molecular Inorganic Chemistry and Catalysis, Inorganic and Structural Chemistry, Center for Molecular Materials, Faculty of Chemistry, Universität Bielefeld, Universitätsstrasse 25, D-33615, Bielefeld, Germany. rghadwal@uni-bielefeld.de.

Dalton Transactions (Cambridge, England : 2003)
|May 16, 2022
PubMed
Summary
This summary is machine-generated.

New phosphino-functionalized mesoionic olefins (p-MIOs) exhibit exceptional basicity, surpassing traditional N-heterocyclic carbenes (NHCs). These compounds readily form dinuclear gold complexes and react with main-group reagents.

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Area of Science:

  • Organometallic Chemistry
  • Main-group Chemistry
  • Carbene Chemistry

Background:

  • Mesoionic carbenes (MIOs) are a class of compounds with unique electronic properties.
  • Phosphino-functionalized ligands offer enhanced coordination capabilities.
  • Understanding the reactivity and properties of novel carbene derivatives is crucial for catalysis and materials science.

Purpose of the Study:

  • To synthesize and characterize novel phosphino-functionalized mesoionic olefins (p-MIOs).
  • To investigate the basicity and electronic properties of these new p-MIOs.
  • To explore the coordination chemistry of p-MIOs with gold and their reactions with main-group electrophiles.

Main Methods:

  • Synthesis of p-MIOs from 1,3-imidazole precursors.
  • Characterization using NMR spectroscopy, X-ray diffraction, and DFT calculations.
  • Reactions with gold precursors and main-group reagents (e.g., PhBCl2).

Main Results:

  • Successful synthesis and characterization of two p-MIOs, 4a and 4b.
  • Demonstrated high proton affinities, indicating superior basicity compared to classical N-heterocyclic carbenes (NHCs).
  • Formation of dinuclear gold complexes with short Au-Au distances and a boronium cation.

Conclusions:

  • Phosphino-functionalization imparts remarkable basicity to mesoionic olefins.
  • p-MIOs serve as effective ligands for gold, forming complexes with interesting structural features.
  • These novel compounds offer potential for applications in catalysis and coordination chemistry.