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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
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Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

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Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

7.9K
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 and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.0K
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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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
3.4K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

2.5K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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Updated: Jun 6, 2025

Chemical Synthesis of Porous Barium Titanate Thin Film and Thermal Stabilization of Ferroelectric Phase by Porosity-Induced Strain
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Promoted Hydride Substitution in BaTiO3 Cubes.

Kazunari Arai1, Kaito Onagi2, Ya Tang1

  • 1Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, 4-12-1, Nakanarusawa, Kyoto, Nishikyo-ku 615-8510, Japan.

Inorganic Chemistry
|November 26, 2024
PubMed
Summary

Researchers synthesized perovskite oxyhydride barium titanate (BaTiO3-H) cubes. Well-defined facets and clean surfaces are crucial for improved hydride content and lower activation energy in these novel materials.

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Area of Science:

  • Materials Science
  • Solid-State Chemistry
  • Nanotechnology

Background:

  • Perovskite oxides are versatile materials with numerous applications.
  • The synthesis of perovskite oxyhydrides, which incorporate hydride anions, presents unique challenges.
  • Controlled morphology and surface chemistry are critical for material properties.

Purpose of the Study:

  • To report the synthesis of perovskite oxyhydride barium titanate (BaTiO3-H) cubes.
  • To investigate the role of surface facets and organic residues in hydride exchange.
  • To determine the activation energy for hydride incorporation in BaTiO3-H.

Main Methods:

  • Topochemical hydride reaction of hydrothermally synthesized barium titanate oxide.
  • X-ray and neutron diffraction for structural analysis.
  • Kissinger analysis to determine activation energy.

Main Results:

  • Successfully synthesized BaTiO3-H cubes (100-300 nm) with improved anion exchange.
  • Achieved a maximum hydride content of 0.7, higher than previously reported.
  • Demonstrated that well-defined {100} facets and absence of organic residues are crucial for hydrogenation.
  • Determined lower activation energy (165 kJ/mol) for BaTiO2.3H0.7 compared to BaTiO2.4H0.6 (313 kJ/mol).

Conclusions:

  • This study presents the first report of perovskite oxyhydrides with well-defined facets.
  • The findings open new avenues for the rational synthesis of oxyhydride materials.
  • Controlled chemical composition and morphology are achievable for advanced oxyhydride applications.