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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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...
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
Mass Spectrometry: Cycloalkene Fragmentation00:54

Mass Spectrometry: Cycloalkene Fragmentation

The molecular ions of cycloalkenes undergo fragmentation via a retro-Diels–Alder reaction.
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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 generated carbocation,...

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Exploiting aggregation to achieve phase separation in macrocyclization.

Anne-Catherine Bédard1, Shawn K Collins

  • 1Département de Chimie, Centre for Green Chemistry and Catalysis, Université de Montréal, CP 6128 Station Downtown, Montréal, Québec H3C 3J7, Canada.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 3, 2013
PubMed
Summary
This summary is machine-generated.

Poly(ethylene glycol) (PEG) aggregation enables high-concentration macrocyclization via Glaser-Hay coupling. This method controls dilution effects, enhancing yield and selectivity through preferential substrate solubilization.

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Area of Science:

  • Organic Chemistry
  • Polymer Chemistry
  • Physical Chemistry

Background:

  • Polymer aggregation properties can influence organic reactions.
  • Controlling dilution effects is crucial for efficient macrocyclization.
  • Glaser-Hay coupling is a common method for forming carbon-carbon bonds.

Purpose of the Study:

  • To investigate the use of poly(ethylene glycol) (PEG) aggregation in organic synthesis.
  • To explore macrocyclization reactions at high concentrations using PEG solvent mixtures.
  • To elucidate the mechanism behind PEG's influence on reaction yield and selectivity.

Main Methods:

  • Utilizing solvent mixtures of poly(ethylene glycol) 400 (PEG(400)) and methanol (MeOH).
  • Performing Glaser-Hay coupling reactions at high substrate concentrations.
  • Employing surface tension measurements, UV spectroscopy, and chemical tagging to study the reaction system.

Main Results:

  • Macrocyclization via Glaser-Hay coupling was successfully conducted at high concentrations using PEG(400)/MeOH mixtures.
  • PEG(400) aggregation was shown to be responsible for the observed control over dilution effects.
  • Preferential solubilization of organic substrates by PEG(400) led to a phase separation from the catalyst, enhancing selectivity and yield.

Conclusions:

  • Poly(ethylene glycol) aggregation offers a novel strategy to overcome dilution limitations in macrocyclization reactions.
  • The selective solubilization and phase separation induced by PEG(400) are key to achieving high yields and selectivity in Glaser-Hay coupling.
  • This approach provides a practical method for conducting complex organic synthesis under concentrated conditions.