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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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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: 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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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.
18.7K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

6.1K
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.
6.1K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.4K
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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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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On Neutral Unsaturated Ouroboric Borylenes.

Kelling J Donald1, Ulrick R Gaillard1, Noah Walker1

  • 1Department of Chemistry, Gottwald Center for the Sciences, University of Richmond, Richmond, Virginia 23173, United States.

The Journal of Physical Chemistry. A
|July 29, 2022
PubMed
Summary
This summary is machine-generated.

Researchers explored stable borylenes, boron analogues of carbenes, for synthetic chemistry. They identified stable five-membered rings with strong singlet preferences and weak aromaticity, offering new avenues for chemical synthesis.

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Area of Science:

  • * Inorganic Chemistry
  • * Theoretical Chemistry
  • * Organic Synthesis

Background:

  • * Borylenes, boron analogues of carbenes, are of interest for synthetic chemistry.
  • * The isolation of stable borylenes remains a significant challenge.

Purpose of the Study:

  • * To investigate the stability and properties of 5- and 6-membered borylenic rings.
  • * To explore the potential of these compounds in modern synthetic chemistry.

Main Methods:

  • * Computational investigation using density functional and ab initio methods.
  • * Analysis of thermochemistry, chemical bonding, and aromaticity.

Main Results:

  • * Several classes of 5- and 6-membered borylenic rings were examined.
  • * Neutral five-membered rings (heterocyclic cyclopentadienyl analogues) show strong singlet multiplicity preferences.
  • * Singlet-triplet gaps exceeding 40 kcal·mol-1 were observed in these systems.
  • * Evidence of weak aromaticity was found in some singlet five-membered and six-membered rings.
  • * Relationships between dative bond length and bond order were identified, reinforced by π-delocalization.

Conclusions:

  • * Stable borylenic ring systems, particularly neutral five-membered analogues, can be designed.
  • * These compounds exhibit significant singlet-triplet energy gaps, indicating stability.
  • * The identified borylenic rings show potential for applications in synthetic chemistry due to their unique electronic properties and aromaticity.