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Related Concept Videos

Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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...
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Olefin cross-metathesis with vinyl halides.

Volodymyr Sashuk1, Cezary Samojłowicz, Anna Szadkowska

  • 1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

Chemical Communications (Cambridge, England)
|May 21, 2008
PubMed
Summary

This study reports the first successful olefin cross-metathesis reaction involving chloroalkenes. This breakthrough expands the scope of alkene functionalization and synthetic chemistry applications.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Olefin metathesis is a powerful carbon-carbon bond-forming reaction.
  • The incorporation of chloroalkenes into cross-metathesis reactions has been challenging.
  • Developing new synthetic routes is crucial for accessing diverse chemical structures.

Purpose of the Study:

  • To demonstrate the first successful olefin cross-metathesis with chloroalkenes.
  • To establish a new synthetic method for functionalizing chloroalkenes.
  • To expand the utility of metathesis reactions in organic synthesis.

Main Methods:

  • Utilized ruthenium-based catalysts for olefin cross-metathesis.
  • Employed chloroalkenes as reaction partners.
  • Optimized reaction conditions including temperature and solvent.

Main Results:

  • Achieved successful cross-metathesis between various chloroalkenes and standard olefins.
  • Demonstrated high yields and selectivity for the desired products.
  • Confirmed the formation of new carbon-carbon bonds with chloroalkene incorporation.

Conclusions:

  • Olefin cross-metathesis with chloroalkenes is feasible.
  • This method provides a novel pathway for synthesizing chlorinated organic compounds.
  • The findings open new avenues for drug discovery and materials science.