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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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.
Cycloaddition Reactions: Overview01:16

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.
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

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).

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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Efficient post-macrocyclization functionalizations of oxacalix[2]arene[2]pyrimidines.

Wim Van Rossom1, Wouter Maes, Lingam Kishore

  • 1Molecular Design and Synthesis, Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium.

Organic Letters
|January 16, 2008
PubMed
Summary

Researchers synthesized diverse oxacalixarene pyrimidines using efficient post-macrocyclization methods. New functional groups were introduced via cross-coupling and nucleophilic substitution reactions on the calixarene skeleton.

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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Oxacalixarenes are macrocyclic compounds with potential applications in molecular recognition and materials science.
  • Developing efficient synthetic routes to functionalized oxacalixarene derivatives is crucial for exploring their properties.

Purpose of the Study:

  • To synthesize diversely functionalized oxacalix[2]arene[2]pyrimidines.
  • To establish efficient post-macrocyclization strategies for modifying oxacalixarene scaffolds.

Main Methods:

  • Synthesis of oxacalix[2]arene[2]pyrimidines from a bis(methylsulfanyl)-substituted oxacalix[4]arene precursor.
  • Liebeskind-Srogl cross-coupling reactions for introducing functionalized aryl groups onto the pyrimidine moiety.
  • Nucleophilic aromatic substitution reactions on a bis(methylsulfonyl)oxacalix[4]arene analogue for modifying the calixarene skeleton with various nucleophiles (O-, S-, N-, C-).

Main Results:

  • Successful synthesis of diversely functionalized oxacalix[2]arene[2]pyrimidines.
  • Demonstration of two efficient post-macrocyclization pathways for molecular diversification.
  • Introduction of a wide range of functional groups onto both the pyrimidine and calixarene units.

Conclusions:

  • The developed synthetic strategies provide access to a library of novel oxacalixarene pyrimidine derivatives.
  • These methods offer versatility for tailoring the properties of oxacalixarene-based molecules for specific applications.