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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.

Acid-Catalyzed Aldol Addition Reaction

Acid-Catalyzed Aldol Addition Reaction

The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.

Intramolecular Aldol Reaction

Intramolecular Aldol Reaction

Intramolecular aldol reaction occurs in dicarbonyl compounds such as dialdehydes, diketones, and keto-aldehydes. The dicarbonyl compounds possess more than one nucleophilic ⍺ carbon for the base to deprotonate and form the enolates. For example, in symmetrical diketones, there are four ⍺ carbons. Hence, four types of enolates are possible when treated with a base. However, since the molecule is symmetrical, the enolates formed on either side of one carbonyl group are equivalent to those...

Aldol Condensation with β-Diesters: Knoevenagel Condensation

Aldol Condensation with β-Diesters: Knoevenagel Condensation

The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).

Base-Catalyzed Aldol Addition Reaction

Base-Catalyzed Aldol Addition Reaction

As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.

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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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Spontaneous and Selective Macrocyclization in Nitroaldol Reaction Systems.

Yunchuan Qi¹, Mubarak Ayinla¹, Stephen Clifford¹

¹Department of Chemistry, University of Massachusetts Lowell, One University Ave., Lowell, Massachusetts 01854, United States.

The Journal of Organic Chemistry

|December 28, 2023

Summary

This summary is machine-generated.

Researchers created lowellane macrocycles using dynamic polymerization and self-sorting in nitroaldol systems. The study explored how building blocks and solvents influence macrocycle formation, with phase-change effects often amplifying results.

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Area of Science:

Organic Chemistry
Supramolecular Chemistry
Polymer Chemistry

Background:

Macrocyclic compounds are crucial in various chemical applications.
Dynamic covalent chemistry enables the construction of complex molecular architectures.
Nitroaldol reactions offer a versatile route to functionalized molecules.

Purpose of the Study:

To efficiently synthesize a range of lowellane macrocycles.
To investigate the influence of building block structure on macrocyclization.
To explore the role of solvent and phase-change effects in macrocycle formation.

Main Methods:

Dynamic polymerization of aromatic dialdehydes and dinitroalkanes.
Self-sorting processes to yield specific macrocyclic structures.
Analysis of macrocycle composition and structural variations.

Main Results:

Efficient generation of lowellane macrocycles with two repeating units (tetra-β-nitroalcohols).
Demonstrated impact of building block structure on macrocyclization efficiency.
Observed amplification of lowellane formation via phase-change effects, with some solution-phase preference.

Conclusions:

Dynamic polymerization and self-sorting are effective for lowellane synthesis.
Building block choice and solvent conditions significantly affect macrocycle formation.
Phase-change effects can be leveraged to enhance macrocyclization yields.