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Related Concept Videos

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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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...
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Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

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In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
7.9K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

8.4K
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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Orthogonal Functionalization of Oxo-Graphene Nanoribbons.

Lucia Merkel1, Christof Neumann2, Christian E Halbig1

  • 1Institute of Chemistry and Biochemistry, Freie Universität Berlin, Altensteinstraße 23a, 14195, Berlin, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 18, 2024
PubMed
Summary

Researchers developed a new orthogonal functionalization method for oxo-graphene nanoribbons (oxo-GNRs). This technique allows for selective modification of both the rims and the π-surface, expanding possibilities for advanced carbon materials.

Keywords:
GrapheneNanoribbonsNanostructuresOrthogonal functionalization

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Area of Science:

  • Materials Science
  • Nanotechnology
  • Organic Chemistry

Background:

  • Oxo-graphene nanoribbons (oxo-GNRs) are derived from the oxidative unzipping of single-walled carbon nanotubes.
  • These nanoribbons possess a high proportion of rim atoms, enabling unique functionalization possibilities.

Purpose of the Study:

  • To present an orthogonal functionalization method for oxo-GNRs.
  • To enable selective functionalization of both the rims and the π-surface of oxo-GNRs.

Main Methods:

  • Orthogonal functionalization strategy applied to oxo-GNRs.
  • X-ray photoelectron spectroscopy (XPS) used for reaction monitoring and marker atom detection.

Main Results:

  • Successful demonstration of orthogonal functionalization on oxo-GNRs.
  • XPS confirmed the selective modification of rims and π-surface.
  • The method's applicability to other oxo-functionalized carbon materials was proposed.

Conclusions:

  • The developed method provides precise control over oxo-GNR functionalization.
  • This strategy is adaptable for graphene quantum dots and reduced graphene oxide.
  • Opens new avenues for tailoring carbon nanomaterials for specific applications.