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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.

Electrophilic Aromatic Substitution: Nitration of Benzene

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Nitriles to Ketones: Grignard Reaction

Nitriles to Ketones: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...

Radical Reactivity: Nucleophilic Radicals

Radical Reactivity: Nucleophilic Radicals

Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

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Published on: August 16, 2018

Taming Tethered Nitreniums for Alkene Functionalization Reactions.

Raju Silver¹, Appasaheb K Nirpal¹, Shyam Sathyamoorthi¹

¹Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.

The Journal of Organic Chemistry

|October 10, 2024

Summary

This study introduces a novel, eco-friendly method for amino-trifluoroacetoxylations of alkenes using N-alkoxy carbamate tethers. This greener approach avoids toxic heavy metals, offering a regioselective and stereospecific transformation.

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Published on: May 26, 2019

Area of Science:

Organic Chemistry
Synthetic Chemistry
Green Chemistry

Background:

Traditional intramolecular amino-hydroxylation methods often rely on toxic heavy metals like osmium.
There is a need for more sustainable and environmentally benign synthetic protocols in organic chemistry.

Purpose of the Study:

To develop a novel, metal-free method for amino-trifluoroacetoxylation of alkenes.
To establish a greener alternative to existing amino-hydroxylation reactions.

Main Methods:

Utilized N-alkoxy carbamate tethers for intramolecular reactions.
Employed hypervalent iodine oxidants to mediate the transformation.
Investigated the reaction's selectivity and stereospecificity with various alkene substrates.

Main Results:

Successfully demonstrated the first examples of amino-trifluoroacetoxylations of alkenes using N-alkoxy carbamate tethers.
The reaction proceeds with high regioselectivity and stereospecificity.
The diastereomeric outcome is dictated by the geometry of the starting alkene.

Conclusions:

Hypervalent iodine mediated amino-trifluoroacetoxylation offers a sustainable and efficient synthetic route.
The reaction mechanism likely involves a transient nitrenium species intermediate.
This method provides a valuable alternative to toxic metal-catalyzed processes.