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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

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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...
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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.
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Reduction of Alkenes: Catalytic Hydrogenation02:13

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

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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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Size and Polarizability as Design Principles for Stereoselective Catalysis.

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  • 1Department of Chemistry, LMU Munich, Butenandtstraße 5-13, 81377, Munich, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
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PubMed
Summary

This study provides molecular volumes and polarizabilities for carbocyclic pi-systems to analyze size-dependent catalysis. These data aid in understanding how increasing substrate or catalyst size impacts reaction rates and stereoselectivity.

Keywords:
London dispersion forcesisotropic polarizabilitymolecular volumenoncovalent interactionsstereoselective catalysis

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Area of Science:

  • Physical Chemistry
  • Organic Chemistry
  • Computational Chemistry

Background:

  • Catalytic processes can exhibit size-dependent behaviors.
  • Understanding the relationship between molecular size and catalytic activity is crucial for optimizing reactions.
  • Carbocyclic pi-systems are fundamental building blocks in organic chemistry and materials science.

Purpose of the Study:

  • To provide molecular volumes and isotropic polarizabilities for a range of carbocyclic pi-systems.
  • To facilitate the analysis of positively size-dependent catalytic processes.
  • To demonstrate the utility of these molecular properties in understanding stereoselective catalysis.

Main Methods:

  • Computational chemistry methods were employed to calculate molecular volumes.
  • Isotropic polarizabilities were computed for various carbocyclic pi-systems.
  • Data were generated for systems ranging from benzene to heptacene.

Main Results:

  • A comprehensive dataset of molecular volumes and isotropic polarizabilities was established.
  • The data spans a significant range of molecular sizes within carbocyclic pi-systems.
  • The calculated properties are suitable for analyzing size-dependent phenomena in catalysis.

Conclusions:

  • The provided molecular properties are valuable for studying size-dependent catalytic effects.
  • This data can enhance the understanding and prediction of reaction rates and stereoselectivity.
  • The approach is applicable to contemporary stereoselective catalytic processes.