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Preparation and Reactions of Sulfides

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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.

Acid Halides to Carboxylic Acids: Hydrolysis

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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...

Acid Halides to Esters: Alcoholysis

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Halide-Accelerated Acyl Fluoride Formation Using Sulfuryl Fluoride.

Paul J Foth¹, Thomas C Malig¹, Hao Yu¹

¹Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.

Organic Letters

|August 19, 2020

Summary

This summary is machine-generated.

A new method uses sulfuryl fluoride (SO₂F₂) for efficient nucleophilic acyl substitution reactions, starting from carboxylic acids. This process, accelerated by halides, yields various acyl derivatives with high efficiency.

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Nucleophilic acyl substitution reactions are fundamental in organic synthesis.
Efficient activation of carboxylic acids is crucial for these transformations.

Purpose of the Study:

To develop a novel one-pot sequential method for nucleophilic acyl substitution reactions.
To utilize sulfuryl fluoride (SO₂F₂) for activating carboxylic acids.

Main Methods:

A one-pot sequential reaction was developed starting from carboxylic acids.
Sulfuryl fluoride (SO₂F₂) was employed for acid activation.
Mechanistic studies investigated the role of anhydrides and acyl fluorides.
Tetrabutylammonium halides were used as accelerators.

Main Results:

SO₂F₂-mediated activation proceeds via anhydrides to form acyl fluorides.
Halide accelerators significantly improved acyl fluoride formation rates.
Acyl fluorides were synthesized in 30-80% yields.
Esters, amides, and thioesters were produced in high yields (72-96%) without reoptimization.

Conclusions:

A new, efficient SO₂F₂-mediated method for nucleophilic acyl substitution has been established.
Halide acceleration provides a robust route to diverse acyl derivatives.
The method offers a versatile platform for synthesizing esters, amides, and thioesters.