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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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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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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.
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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...
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Oxidation of Electron-Rich Arenes Using HFIP-UHP System.

Natalia Llopis1, Alejandro Baeza1

  • 1Departamento de Quı́mica Orgánica and Instituto de Sı́ntesis Orgánica (ISO), Facultad de Ciencias, Universidad de Alicante, Apdo. 99, Alicante E-03080, Spain.

The Journal of Organic Chemistry
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This study presents a green oxidation method for electron-rich arenes like phenols and naphthols using a hexafluoroisopropanol-urea hydrogen peroxide system. The process efficiently yields valuable quinones and hydroxylated arenes under mild conditions.

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Area of Science:

  • Organic Chemistry
  • Green Chemistry

Background:

  • Oxidation of electron-rich arenes is crucial for synthesizing valuable organic compounds.
  • Developing environmentally benign oxidation methods is a key challenge in organic synthesis.

Purpose of the Study:

  • To develop a straightforward and eco-friendly method for oxidizing electron-rich arenes.
  • To achieve moderate to good yields of quinones and hydroxylated arenes.

Main Methods:

  • Utilizing an environmentally benign system comprising hexafluoroisopropanol (HFIP) and urea hydrogen peroxide (UHP).
  • Applying mild reaction conditions for the oxidation process.

Main Results:

  • Successful oxidation of phenols, naphthols, and anisole derivatives.
  • Obtained corresponding quinones or hydroxylated arenes in moderate to good yields.

Conclusions:

  • The HFIP-UHP system offers an efficient and green approach for arene oxidation.
  • This method provides a sustainable route to important aromatic compounds.