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Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

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.

Alcohols from Carbonyl Compounds: Reduction

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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 reactions,...

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

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.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.

Hydrogen Bonds

Hydrogen Bonds

Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....

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A Simple, Low-cost, and Robust System to Measure the Volume of Hydrogen Evolved by Chemical Reactions with Aqueous Solutions

A Simple, Low-cost, and Robust System to Measure the Volume of Hydrogen Evolved by Chemical Reactions with Aqueous Solutions

Published on: August 17, 2016

Solid Aluminum Borohydrides for Prospective Hydrogen Storage.

Iurii Dovgaliuk^1,2, Damir A Safin¹, Nikolay A Tumanov¹

¹Institute of Condensed Matter and Nanosciences, Université catholique de Louvain, Place L. Pasteur 1, 1348, Louvain-la-Neuve, Belgium.

|October 6, 2017

Summary

New aluminum borohydride compounds offer improved stability for hydrogen storage. These solid-state materials are safer and more practical than previous aluminum borohydride forms, advancing research in energy storage solutions.

Keywords:

aluminum crystal structures high-energy materials hydrides hydrogen storage

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Hydrogen Charging of Aluminum using Friction in Water

Hydrogen Charging of Aluminum using Friction in Water

Published on: January 28, 2020

Area of Science:

Materials Science
Inorganic Chemistry
Energy Storage

Background:

Metal borohydrides are key materials for high-capacity hydrogen storage.
Aluminum borohydride (Al(BH4)3) offers high hydrogen content but suffers from poor stability and safety issues.
There is a need for stable and practical aluminum-based hydrogen storage materials.

Purpose of the Study:

To investigate a new family of mixed-cation aluminum borohydrides, M[Al(BH4)4].
To evaluate their thermal decomposition behaviors and stability for hydrogen storage applications.
To determine their potential in advancing hydrogen storage technologies.

Main Methods:

Synthesis and characterization of M[Al(BH4)4] compounds.
Thermal decomposition analysis under various conditions.
Correlation of decomposition temperatures with cation properties (ionic potential).

Main Results:

Mixed-cation compounds M[Al(BH4)4] are stable solids at ambient conditions.
Diverse decomposition pathways observed, releasing either Al(BH4)3 or hydrogen and diborane depending on the cation M.
Ammonium aluminum borohydride (NH4[Al(BH4)4]) exhibits the lowest decomposition temperature (35°C).
Decomposition temperatures fall within a practical stability window, influenced by cation ionic potential.

Conclusions:

The M[Al(BH4)4] family presents a promising class of solid-state hydrogen storage materials.
These compounds offer improved stability and handling compared to Al(BH4)3.
This research advances aluminum borohydride chemistry for practical hydrogen storage, including reactive hydride composites.