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Acid Halides to Ketones: Gilman Reagent

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...

Mixtures of Acids

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The pH of a solution containing an acid can be determined using its acid dissociation constant and initial concentration. If a solution contains two different acids, then its pH can be determined using one of several methods depending on the relative strength of the acids and their dissociation constants.
In a strong and weak acid mixture, the strong acid dissociates completely and becomes a source of almost all the hydronium ions present in the solution. In contrast, the weak acid shows...

Mixtures of Acids

Mixtures of Acids

The pH of a solution containing an acid can be determined using its acid dissociation constant and its initial concentration. If a solution contains two different acids, then its pH can be determined using one of several methods depending upon the relative strength of the acids and their dissociation constants.
A Mixture of a Strong Acid and a Weak Acid
In a mixture of a strong acid and a weak acid, the strong acid dissociates completely and becomes a source of almost all the hydronium ions...

Acid Halides to Amides: Aminolysis

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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...

Acid Halides to Esters: Alcoholysis

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Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:

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One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...

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Selected applications of Meldrum's acid - a tutorial.

Felix Brosge¹, Pardeep Singh¹, Fredrik Almqvist¹

¹Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany. carsten.bolm@oc.rwth-aachen.de.

Organic & Biomolecular Chemistry

|May 21, 2021

Summary

This summary is machine-generated.

Meldrum's acid is a versatile molecule with unique chemical properties, including a low pKa and reactivity at multiple positions. This review provides a broad overview of its synthetic chemistry for researchers and students.

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Meldrum's acid possesses a unique structure enabling diverse chemical transformations.
Its notable properties include a low pKa (~4.9) in water and distinct reactivity at C4, C5, and C6 positions.

Purpose of the Study:

To provide a comprehensive overview of Meldrum's acid synthetic chemistry.
To equip students and researchers with essential knowledge for designing and synthesizing novel compounds.
To highlight recent advances and stimulate further research into Meldrum's acid applications.

Main Methods:

Review of established and recent synthetic methodologies involving Meldrum's acid.
Discussion of electrophilic and nucleophilic substitution reactions at Meldrum's acid core.
Exploration of thermal decomposition pathways for cycloaddition and acylation reactions.

Main Results:

Meldrum's acid readily undergoes electrophilic substitution at C5 and nucleophilic attack at C4/C6.
Distinct thermal decomposition pathways facilitate cycloaddition and acylation reactions.
Recent advancements showcase the utility of Meldrum's acid derivatives in various synthetic scenarios.

Conclusions:

Meldrum's acid is a highly relevant and synthetically flexible molecule.
Understanding its diverse reactivity is crucial for developing new chemical entities.
Continued exploration promises innovative applications in organic synthesis.