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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.

Formation of Halohydrin from Alkenes

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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.

Conformations of Butane

Conformations of Butane

Unlike ethane and propane that have only two major conformations, butane has more than two conformers. The staggered form of butane in which the bulky methyl groups on the two carbons are placed on opposite sides, that is, at a dihedral angle of 180°, is the lowest energy, most stable form — called the anti conformer. This conformation is stabilized due to the absence of steric repulsion between the largely spaced out methyl groups. The other two staggered conformations are degenerate and have...

Preparation of Diols and Pinacol Rearrangement

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

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Updated: Jun 1, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

Butallyl-onal 1,4-dioxane hemisolvate.

Thomas Gelbrich¹, Denise Rossi, Ulrich J Griesser

¹Institute of Pharmacy, University of Innsbruck, Innrain 52, 6020 Innsbruck, Austria.

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This summary is machine-generated.

This study details the crystal structure of butallyl-onal and 1,4-dioxane, revealing a unique ladder-like arrangement. The barbiturate and dioxane molecules form an intricate network through hydrogen bonding, creating a stable supramolecular structure.

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Published on: November 9, 2019

Area of Science:

Crystallography
Supramolecular Chemistry
Organic Chemistry

Background:

Barbiturate derivatives are known for their diverse pharmacological activities.
Understanding the solid-state structure of such compounds is crucial for predicting their properties and designing new molecules.
1,4-dioxane is a common solvent and can participate in crystal lattice formation.

Purpose of the Study:

To elucidate the crystal structure of the 1:0.5 solvate of 5-(1-bromo-prop-2-en-1-yl)-5-sec-butyl-pyrimidine-2,4,6-trione (butallyl-onal) with 1,4-dioxane.
To investigate the intermolecular interactions and packing arrangement in the solid state.
To characterize the hydrogen bonding network formed between butallyl-onal and 1,4-dioxane molecules.

Main Methods:

Single-crystal X-ray diffraction analysis was performed.
The crystal structure was solved and refined.
Intermolecular interactions, including hydrogen bonds, were analyzed.

Main Results:

The asymmetric unit contains one molecule of butallyl-onal and half a molecule of 1,4-dioxane.
The barbiturate ring of butallyl-onal is nearly planar, with the largest deviation from the mean plane being 0.049(5) Å.
The 1,4-dioxane molecule adopts a nearly ideal chair conformation.
Barbiturate molecules form single-stranded chains via N-H⋯O hydrogen bonds.
1,4-dioxane molecules act as bridges, connecting anti-parallel barbiturate chains through N-H⋯O(dioxane) hydrogen bonds, forming a ladder-like structure.

Conclusions:

The crystal structure reveals a unique ladder-like supramolecular architecture formed by butallyl-onal and 1,4-dioxane.
This arrangement is stabilized by a specific network of hydrogen bonds.
The study provides insights into the solid-state behavior of butallyl-onal and its interactions with solvents.