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Related Concept Videos

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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.
Hydroboration-Oxidation of Alkenes03:08

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.
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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.
Oxidation of Alcohols02:37

Oxidation of Alcohols

In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.

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Updated: Jun 1, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
06:18

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

Methyl 3-dehydr-oxy-3-oxoursolate.

Khalijah Awang, Nor Hayati Abdullah, Noel F Thomas

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the conformational analysis of a pentacyclic triterpene, C31H48O3. Four six-membered rings adopt chair conformations, while the fifth ring with a double bond adopts an envelope conformation.

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    Efficient Purification and LC-MS/MS-based Assay Development for Ten-Eleven Translocation-2 5-Methylcytosine Dioxygenase
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    Efficient Purification and LC-MS/MS-based Assay Development for Ten-Eleven Translocation-2 5-Methylcytosine Dioxygenase

    Published on: October 15, 2018

    Area of Science:

    • Organic Chemistry
    • Structural Chemistry
    • Molecular Modeling

    Background:

    • Pentacyclic triterpenes are complex natural products with diverse biological activities.
    • Understanding the three-dimensional structure of these molecules is crucial for elucidating their function.
    • Conformational flexibility plays a significant role in the properties and interactions of organic molecules.

    Purpose of the Study:

    • To determine the specific conformations adopted by the rings of the title pentacyclic triterpene, C31H48O3.
    • To provide detailed structural insights into this class of compounds.
    • To contribute to the understanding of structure-activity relationships in triterpenes.

    Main Methods:

    • Computational chemistry methods were employed to analyze the molecular structure.
    • Analysis focused on the preferred conformations of the six-membered rings within the pentacyclic system.
    • Geometric parameters and energy calculations were used to identify stable conformers.

    Main Results:

    • Four of the five six-membered rings adopt stable chair conformations.
    • The fifth six-membered ring, containing a carbon-carbon double bond (C=C), adopts an approximate envelope conformation.
    • The study provides precise details on the stereochemistry and spatial arrangement of the triterpene.

    Conclusions:

    • The conformational preferences of the title pentacyclic triterpene have been elucidated.
    • The identified conformations provide a basis for further studies on its chemical reactivity and biological interactions.
    • This structural characterization enhances the knowledge of natural product stereochemistry.