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Related Concept Videos

Isomerism in Alkenes02:01

Isomerism in Alkenes

Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
E1 Reaction: Stereochemistry and Regiochemistry02:43

E1 Reaction: Stereochemistry and Regiochemistry

One of the critical aspects of the E1 reaction mechanism, as also observed in E2, is the regiochemistry, with multiple regioisomers obtained as products. In the example discussed, the presence of water as a weak base favors elimination over substitution to generate two alkenes. Given that alkenes’ stability increases with the number of alkyl groups across the double bond, typically, E1 reactions lead to the Zaitsev product, for this is more substituted and stable than the Hofmann product.
E2 Reaction: Stereochemistry and Regiochemistry02:43

E2 Reaction: Stereochemistry and Regiochemistry

Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major product and...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Stereoselective alkene isomerization over one position.

Casey R Larsen1, Douglas B Grotjahn

  • 1Department of Chemistry and Biochemistry, San Diego State University, San Diego, California 92182-1030, USA.

Journal of the American Chemical Society
|June 19, 2012
PubMed
Summary
This summary is machine-generated.

This study introduces catalyst 1, a highly efficient solution for selective alkene isomerization. It rapidly produces over 99.5% E-alkene products with exceptional kinetic selectivity, even for sensitive substrates.

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Stereoselective Synthesis

Background:

  • Alkene isomerization presents challenges in controlling double bond position and E:Z selectivity.
  • Developing efficient catalysts for selective transformations is crucial in organic synthesis.

Purpose of the Study:

  • To introduce and evaluate catalyst 1 for selective mono-isomerization of multifunctional alkenes.
  • To demonstrate the high efficiency and selectivity of catalyst 1 under mild conditions.

Main Methods:

  • Utilized catalyst 1 for the isomerization of various multifunctional alkenes.
  • Performed reactions at room temperature with low catalyst loadings (0.01-0.1 mol%).
  • Analyzed reaction kinetics and product selectivity using analytical techniques.

Main Results:

  • Achieved >99.5% E-product selectivity in alkene isomerization.
  • Demonstrated rapid reaction completion (within 10 min) at room temperature.
  • Showcased catalyst 1's ability to generate sensitive enols and enamides.
  • Observed extremely high kinetic selectivity, with E-to-Z isomerization being <10(-6) times the rate of formation.

Conclusions:

  • Catalyst 1 is a highly efficient and selective catalyst for alkene isomerization.
  • The catalyst enables the synthesis of valuable E-alkene products under mild and rapid conditions.
  • Catalyst 1 offers significant advantages for synthesizing complex molecules with sensitive functional groups.