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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.3K
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

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

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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...
16.1K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

9.4K
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.
9.4K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

10.1K
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.
10.1K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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...
3.8K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

13.8K
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...
13.8K

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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

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CF2-Driven Regioselectivity in C70 Hydrogenation.

Nikita A Malkin1, Victor A Brotsman1, Natalia S Lukonina1

  • 1Chemistry Department, M.V.Lomonosov Moscow State University, Moscow, Russia.

Chempluschem
|November 20, 2025
PubMed
Summary
This summary is machine-generated.

This study models the hydrogenation of C70 fullerene derivatives with CF2 groups. Researchers synthesized and characterized new C70(CF2)H2 isomers, revealing insights into fullerene reactivity and hydrogenation suppression.

Keywords:
carbanionsdifluoromethylenefullereneshydrogenationregioselectivity

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Area of Science:

  • Fullerene Chemistry
  • Organic Synthesis
  • Computational Chemistry

Background:

  • Fullerenes like C70 are carbon allotropes with unique electronic properties.
  • Functionalization of fullerenes, such as with CF2 groups, can alter their reactivity.
  • Understanding hydrogenation pathways is crucial for fullerene applications.

Purpose of the Study:

  • To theoretically model the reductive hydrogenation of various C70(CF2) isomers.
  • To regioselectively synthesize and characterize novel C70(CF2)H2 isomers.
  • To investigate the factors influencing hydrogenation regioselectivity and reactivity.

Main Methods:

  • Theoretical modeling of reductive hydrogenation.
  • Regioselective synthesis of C70(CF2)H2 isomers.
  • Spectral characterization (Mass Spectrometry, UV/Vis, FTIR, Raman, NMR).

Main Results:

  • Identified activated bridgehead carbon atoms in the anionic state prone to protonation.
  • Synthesized three novel C70(CF2)H2 isomers (I-III).
  • Observed suppression of C70 hydrogenation in the presence of C70(CF2) and high reactivity of near-equatorial isomers.

Conclusions:

  • The position and configuration of the CF2 moiety influence hydrogenation regioselectivity.
  • Theoretical and experimental data provide insights into fullerene hydrogenation mechanisms.
  • Findings contribute to understanding fullerene functionalization and reactivity for potential applications.