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Related Concept Videos

Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

9.0K
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...
9.0K
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
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 Dehydration of Alcohols to Alkenes02:35

Acid-Catalyzed Dehydration of Alcohols to Alkenes

23.9K
In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
23.9K
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
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

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Updated: Jan 30, 2026

Utilizing the Ethylene-releasing Compound, 2-Chloroethylphosphonic Acid, as a Tool to Study Ethylene Response in Bacteria
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Utilizing the Ethylene-releasing Compound, 2-Chloroethylphosphonic Acid, as a Tool to Study Ethylene Response in Bacteria

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Gold-catalyzed ethylene cyclopropanation.

Silvia G Rull1, Andrea Olmos1, Pedro J Pérez1

  • 1Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva, Campus de El Carmen 21007 Huelva, Spain.

Beilstein Journal of Organic Chemistry
|January 26, 2019
PubMed
Summary

Ethylene can be directly converted into ethyl 1-cyclopropylcarboxylate using ethyl diazoacetate and a catalytic system. This gold-catalyzed reaction offers a novel pathway for synthesizing cyclopropyl carboxylates.

Keywords:
carbene transfercyclopropanecyclopropylcarboxylateethyl diazoacetateethylene cyclopropanationgold catalysis

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Ethylene Polymerizations Using Parallel Pressure Reactors and a Kinetic Analysis of Chain Transfer Polymerization
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Ethylene Polymerizations Using Parallel Pressure Reactors and a Kinetic Analysis of Chain Transfer Polymerization

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Direct functionalization of alkenes remains a significant challenge in organic chemistry.
  • Development of efficient catalytic systems for C-H functionalization is highly desirable.

Purpose of the Study:

  • To develop a novel method for the direct conversion of ethylene to ethyl 1-cyclopropylcarboxylate.
  • To explore the utility of gold catalysis in alkene functionalization reactions.

Main Methods:

  • Reaction of ethylene with ethyl diazoacetate (EDA).
  • Utilized catalytic amounts of IPrAuCl/NaBArF 4 as the catalytic system.
  • Characterization of the product using standard spectroscopic techniques.

Main Results:

  • Direct conversion of ethylene to ethyl 1-cyclopropylcarboxylate was achieved with high efficiency.
  • The catalytic system demonstrated excellent activity and selectivity.
  • The reaction proceeded under mild conditions.

Conclusions:

  • A novel and efficient gold-catalyzed method for the synthesis of ethyl 1-cyclopropylcarboxylate from ethylene has been established.
  • This methodology provides a valuable new route for constructing cyclopropane rings.
  • The catalytic system shows promise for broader applications in alkene functionalization.