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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.

Hybridization of Atomic Orbitals I

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...

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...

π Molecular Orbitals of 1,3-Butadiene

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the...

Radical Substitution: Allylic Bromination

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

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Related Experiment Video

Updated: Apr 18, 2026

Photoselective Vaporesection of the Prostate via an End-firing Lithium Triborate Crystal Laser

Photoselective Vaporesection of the Prostate via an End-firing Lithium Triborate Crystal Laser

Published on: May 9, 2018

A borane laser.

Luis Cerdán¹, Jakub Braborec², Inmaculada Garcia-Moreno¹

¹Department of Low Dimensional Systems, Surfaces and Condensed Matter, Instituto de Química-Física 'Rocasolano', Consejo Superior de Investigaciones Científicas (CSIC), Serrano 119, ES-28006 Madrid, Spain.

Nature Communications

|January 14, 2015

Summary

This summary is machine-generated.

Researchers developed a novel blue laser material from boron hydrides, offering a stable and efficient alternative to current organic and nanocrystal options. This discovery unlocks boranes as a new resource for laser technology.

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Area of Science:

Materials Science
Optoelectronics
Inorganic Chemistry

Background:

Commercially available solution-processed blue lasers rely on organic compounds or semiconductor nanocrystals.
These materials often suffer from poor solubility, low stability (chemical and photo-), and high costs.
There is a need for competitive and stable alternatives for blue laser applications.

Purpose of the Study:

To introduce a novel class of inorganic cluster compounds, specifically boron hydrides, as a competitive alternative for blue-emitting laser materials.
To demonstrate the laser emission properties and photostability of a specific borane compound.

Main Methods:

Solution processing of the borane anti-B18H22.
Pulsed laser excitation of the borane solution.
Characterization of emission wavelength, efficiency, and photostability.

Main Results:

Demonstrated blue laser emission at 406 nm from anti-B18H22 solutions under pulsed excitation.
Achieved a notable energy conversion efficiency of 9.5% (output/input).
Exhibited superior photostability compared to many state-of-the-art commercial blue laser dyes.

Conclusions:

Boron hydrides represent a novel and competitive class of materials for blue laser applications.
The borane anti-B18H22 shows promising performance metrics, including efficiency and photostability.
This research opens avenues for developing new laser materials from the largely untapped field of borane chemistry.