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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

11.8K
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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Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

Autoxidation of Ethers to Peroxides and Hydroperoxides

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Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

11.3K
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.
11.3K
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

5.1K
Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is activated by...
5.1K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.6K
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.
9.6K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

7.6K
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.
7.6K

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A Facile Synthetic Method to Obtain Bismuth Oxyiodide Microspheres Highly Functional for the Photocatalytic Processes of Water Depuration
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The quest for beryllium peroxides.

R J Berger1, M Hartmann, P Pyykkö

  • 1Anorganisch-chemisches Institut, Technische Universität München, Lichtenbergstrasse 4, D-85747 Garching, Germany.

Inorganic Chemistry
|May 1, 2001
PubMed
Summary
This summary is machine-generated.

Beryllium peroxide compounds lack experimental proof. Quantum chemical calculations suggest potential stability in nonaqueous media, but not in aqueous solutions where water competes effectively.

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Area of Science:

  • Inorganic Chemistry
  • Quantum Chemistry
  • Materials Science

Background:

  • No experimental evidence exists for beryllium peroxide compounds in scientific literature.
  • Previous preparative attempts using beryllium salts and peroxides under mild conditions have been unsuccessful.
  • Aqueous solution studies involving beryllium salts and hydrogen peroxide also failed to detect peroxoberyllate species.

Purpose of the Study:

  • To investigate the theoretical feasibility and structural properties of various beryllium peroxide model compounds.
  • To understand the energetics and bonding characteristics of potential beryllium peroxide species.
  • To explore the stability of beryllium peroxides in both aqueous and nonaqueous environments.

Main Methods:

  • Experimental attempts to synthesize beryllium peroxides using various beryllium salts and peroxides.
  • Nuclear Magnetic Resonance (NMR) spectroscopy ((1)H and (9)Be) to analyze aqueous solutions.
  • Quantum chemical calculations, including Hartree-Fock and density functional theory, to model gas-phase beryllium peroxide compounds.

Main Results:

  • Experimental synthesis attempts and aqueous NMR studies yielded no evidence for beryllium peroxides.
  • Quantum chemical calculations predicted stable structures for several beryllium peroxide models, including mononuclear and binuclear species.
  • Calculations indicated that Be-O(peroxide) bonds are relatively weak, and peroxide groups are unlikely to displace water or hydroxide in aqueous solutions.
  • Predicted structures represent local minima and are potentially (meta)stable in nonaqueous media.

Conclusions:

  • Beryllium peroxides are not observed in aqueous solutions due to the strong competition from water and hydroxide ions.
  • Theoretical models suggest that beryllium peroxide compounds could be stable in nonaqueous environments.
  • The findings highlight a gap in experimental verification, similar to aluminum peroxides, possibly linked to their diagonal relationship in the periodic table.