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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.6K
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.
2.6K
Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

2.5K
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.
2.5K
Intramolecular Aldol Reaction01:18

Intramolecular Aldol Reaction

2.1K
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...
2.1K
Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

Aldol Condensation with β-Diesters: Knoevenagel Condensation

3.0K
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.
3.0K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.2K
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).
2.2K
Base-Catalyzed Aldol Addition Reaction01:08

Base-Catalyzed Aldol Addition Reaction

3.4K
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.
3.4K

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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
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Summary

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.