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Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

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The Synthesis of RGD-functionalized Hydrogels as a Tool for Therapeutic Applications

The Synthesis of RGD-functionalized Hydrogels as a Tool for Therapeutic Applications

Published on: October 7, 2016

Oscillatory carbonylation using alkyne-functionalised poly(ethylene glycol).

Lynn Donlon¹, Katarina Novakovic

¹Department of Chemical Engineering and Advanced Materials, Newcastle University, Merz Court, Newcastle, NE1 7RU, UK. katarina.novakovic@ncl.ac.uk.

Chemical Communications (Cambridge, England)

|June 25, 2014

Summary

Palladium-catalyzed oscillatory carbonylation was achieved using poly(ethylene glycol) substrates. This study recorded synchronized pH and turbidity oscillations over several days, proposing a reaction network to explain these phenomena.

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Anionic Polymerization of an Amphiphilic Copolymer for Preparation of Block Copolymer Micelles Stabilized by π-π Stacking Interactions

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Published on: October 10, 2016

Area of Science:

Chemical Sciences
Polymer Chemistry
Catalysis

Background:

Oscillatory reactions offer unique insights into complex chemical dynamics.
Palladium catalysis is crucial for various organic transformations, including carbonylation.
Poly(ethylene glycol) (PEG) derivatives are widely used in materials science and drug delivery.

Purpose of the Study:

To achieve and characterize palladium-catalyzed oscillatory carbonylation reactions.
To investigate the use of mono alkyne-terminated poly(ethylene glycol) methyl ether substrates in such reactions.
To propose a mechanistic understanding of the observed oscillations.

Main Methods:

Utilizing palladium catalysis for carbonylation reactions.
Employing mono alkyne-terminated poly(ethylene glycol) methyl ether as substrates.
Monitoring reaction progress through synchronized measurements of pH and solution turbidity over extended periods.

Main Results:

Successfully demonstrated palladium-catalyzed oscillatory carbonylation.
Achieved reproducible and synchronized oscillations in pH and solution turbidity.
Observed these oscillations consistently over several days of reaction time.

Conclusions:

The study successfully established a novel oscillatory carbonylation system.
The proposed reaction network provides a plausible explanation for the observed dynamic behavior.
This work opens avenues for developing new catalytic systems with predictable oscillatory outputs.