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Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.

Pericyclic Reactions: Introduction

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...

Cycloaddition Reactions: MO Requirements for Thermal Activation

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.

Reactions of Carboxylic Acids: Introduction

Reactions of Carboxylic Acids: Introduction

Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Woodward–Hoffmann Selection Rules and Microscopic Reversibility

Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...

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Coarctate cyclization reactions: a primer.

Brian S Young¹, Rainer Herges, Michael M Haley

¹University of Oregon-Department of Chemistry, Eugene, Oregon 97403-1253, USA.

Chemical Communications (Cambridge, England)

|August 1, 2012

Summary

This summary is machine-generated.

Researchers explored the reverse reaction of forming heterocycles from conjugated ene-ene-yne systems using coarctate chemistry. This novel approach utilizes triazene-arene-alkynes for efficient heterocycle synthesis.

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Published on: September 18, 2016

Area of Science:

Organic Chemistry
Synthetic Chemistry
Reaction Mechanisms

Background:

The cleavage of five-membered heterocycles to form ene-ene-yne systems is well-established.
The reverse synthesis of heterocycles from ene-ene-yne precursors is a recent development.
Coarctate reactions represent an unusual class of concerted reactions.

Purpose of the Study:

To detail synthetic and mechanistic studies on heterocycle formation.
To investigate the cyclization of "hetero-ene-ene-yne" motifs.
To explore the application of coarctate chemistry in generating heterocycles.

Main Methods:

Computational studies of coarctate reactions.
Experimental synthesis of triazene-arene-alkynes and related systems.
Mechanistic investigations of the cyclization process.

Main Results:

Demonstrated the feasibility of forming heterocycles from ene-ene-yne precursors.
Elucidated the mechanism of coarctate reactions in this context.
Successfully synthesized various heterocycles using this novel approach.

Conclusions:

Coarctate chemistry provides an effective route for heterocycle synthesis.
The study expands the synthetic utility of conjugated ene-ene-yne systems.
This work offers new insights into concerted reaction mechanisms.