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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

8.0K
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.
8.0K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.8K
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...
1.8K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.1K
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...
8.1K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

17.9K
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.
17.9K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

11.9K
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
11.9K
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

4.4K
Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials
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Pressure Strategy To Improve H Atomic Utilization via Optimized Decomposition Pathway in Solid Hydrazine Borane.

Libo Sheng1, Guangyu Qi1, Kaixiang Jin1

  • 1State Key Laboratory of Superhard Materials, College of Physics, Jilin University, Changchun 130012, China.

The Journal of Physical Chemistry Letters
|September 23, 2024
PubMed
Summary

High pressure enhances hydrogen storage in hydrazine borane (HB) by over 95% atomic utilization. This method optimizes HB decomposition, preventing hydrazine loss and enabling superconductor synthesis.

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Area of Science:

  • Materials Science
  • Chemistry

Background:

  • Hydrazine borane (N2H4BH3, HB) is a promising hydrogen storage material due to its high hydrogen content (15.4 wt%).
  • Solid HB pyrolysis at ambient pressure results in significant mass loss (~30 wt%) due to hydrazine (N2H4) evolution, limiting its efficiency.

Purpose of the Study:

  • To investigate the effect of high pressure on the decomposition pathway of solid hydrazine borane.
  • To optimize the hydrogen release process and improve atomic utilization in HB.

Main Methods:

  • High-pressure pyrolysis of solid hydrazine borane.
  • Energy-dispersive spectroscopy (EDS) for elemental analysis.
  • In-situ high-pressure-high-temperature Raman and Infrared (IR) spectroscopy.
  • Density functional theory (DFT) calculations and Hirshfeld analysis.

Main Results:

  • High pressure acts as a catalyst, optimizing the decomposition pathway of solid HB.
  • Pressure significantly inhibits the evolution of hydrazine (N2H4), improving H atomic utilization to over 95%.
  • Spectroscopic and computational analyses reveal pressure-enhanced dihydrogen and BN bonds contribute to this inhibition.

Conclusions:

  • High pressure is an effective strategy to enhance hydrogen storage and release from hydrazine borane.
  • Optimized HB decomposition under pressure makes it a viable hydrogen source for advanced material synthesis, such as the superconductor CeH9.