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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

Diels–Alder Reaction: Characteristics of Dienes

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

Diels–Alder Reaction: Characteristics of Dienophiles

Diels–Alder Reaction: Characteristics of Dienophiles

In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction.
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...

Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors

Diels–Alder vs Retro-Diels–Alder Reaction: Thermodynamic Factors

The Diels–Alder reaction is thermally reversible, meaning that the reaction reverts to the starting diene and dienophile under suitable temperatures. The forward reaction gives a cyclohexene derivative and is favored at low to medium temperatures. The reverse process, also called retro-Diels–Alder reaction, is a ring-opening process favored at high temperatures.

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Davis-Beirut Reaction Inspired Nitroso Diels-Alder Reaction.

Jung-Ho Son¹, Amy Cheung¹, Jie S Zhu¹

¹Department of Chemistry, University of California, Davis, One Shields Ave., Davis, CA 95616.

Tetrahedron Letters

|April 15, 2021

Summary

A novel one-pot nitroso Diels-Alder reaction protocol was developed. This method efficiently synthesizes aryldihydro-1,2-oxazines from readily available nitrophenyl starting materials, offering a new synthetic route.

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

The Davis-Beirut reaction is a known chemical transformation.
Nitroso Diels-Alder reactions are valuable for synthesizing heterocyclic compounds.

Purpose of the Study:

To develop a novel one-pot protocol for synthesizing aryldihydro-1,2-oxazines.
To adapt a Davis-Beirut reaction inspired approach for nitroso Diels-Alder chemistry.

Main Methods:

Utilizing nitrophenyl compounds with para-substituted 2°-amine or 2°-alcohol.
Employing a one-pot procedure involving deprotonation, oxidation, and reduction.
Generating a nitrosophenyl intermediate for subsequent cyclization.

Main Results:

Successful synthesis of aryldihydro-1,2-oxazines.
Moderate yields achieved through the developed one-pot protocol.
Demonstration of a new application of Davis-Beirut reaction principles.

Conclusions:

The reported protocol offers an efficient one-pot method for aryldihydro-1,2-oxazine synthesis.
This approach provides a valuable alternative for constructing nitrogen-containing heterocycles.