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Related Concept Videos

Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

8.9K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
8.9K
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

10.2K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
10.2K
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

3.3K
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.
3.3K
Acid-Catalyzed Hydration of Alkenes02:45

Acid-Catalyzed Hydration of Alkenes

17.2K
Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.
17.2K
Base-Catalyzed Aldol Addition Reaction01:08

Base-Catalyzed Aldol Addition Reaction

4.5K
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.
4.5K
Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

3.3K
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.
3.3K

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Teratoma Generation in the Testis Capsule
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Cyclizations catalyzed inside a hexameric resorcinarene capsule.

Yujie Zhu1, Julius Rebek Jr, Yang Yu

  • 1Center for Supramolecular Chemistry & Catalysis and Department of Chemistry, College of Science, Shanghai University, 99 Shang-Da Road, Shanghai 200444, China. yangyu2017@shu.edu.cn.

Chemical Communications (Cambridge, England)
|March 9, 2019
PubMed
Summary
This summary is machine-generated.

The resorcin[4]arene capsule, a self-assembled host, excels in container catalysis by stabilizing charged intermediates. It is particularly effective for catalyzing various cyclization reactions, showcasing its versatility in organic synthesis.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Catalysis
  • Host-Guest Chemistry

Background:

  • The resorcin[4]arene capsule is a readily accessible self-assembled host system.
  • It stabilizes cationic intermediates and transition states via cation-π interactions.
  • Container catalysis offers a unique environment for chemical transformations.

Purpose of the Study:

  • To highlight the applications of the resorcin[4]arene capsule in catalysis.
  • To focus on its utility in promoting cyclization reactions.
  • To demonstrate the potential of host systems in organic synthesis.

Main Methods:

  • Utilizing the self-assembled hexameric resorcin[4]arene capsule as a catalytic host.
  • Employing cation-π interactions for stabilization of intermediates.
  • Investigating cyclization reactions within the capsule's cavity.

Main Results:

  • The resorcin[4]arene capsule effectively catalyzes terpene cyclizations.
  • Intramolecular hydroalkoxylation reactions are successfully performed.
  • Carbonyl-olefin metathesis is demonstrated within the host system.

Conclusions:

  • The resorcin[4]arene capsule is a powerful tool for container catalysis.
  • It facilitates challenging cyclization reactions through intermediate stabilization.
  • This host system holds significant promise for advancing organic synthesis.