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Related Concept Videos

Preparation of Diols and Pinacol Rearrangement01:57

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.
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.
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 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.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

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Octa-butylbis[μ(2)-4-(diethyl-amino)-benzoato-κO:O']bis-[4-(diethyl-amino)-benzoato-κO]di-μ(3)-oxido-tetra-tin(IV).

Acta crystallographica. Section E, Structure reports online·2011
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Bis(μ(2)-2-amino-5-nitro-benzoato)bis-(2-amino-5-nitro-benzoato)octa-butyldi-μ(3)-oxido-tetra-tin(IV).

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(5E)-5-(4-Meth-oxy-benzyl-idene)-2-(piperidin-1-yl)-1,3-thia-zol-4(5H)-one.

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Related Experiment Video

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

2-Hy-droxy-2-(3-oxobutan-2-yl)indan-1,3-dione.

Raza Murad Ghalib, Rokiah Hashim, Sayed Hasan Mehdi

    Acta Crystallographica. Section E, Structure Reports Online
    |August 13, 2011
    PubMed
    Summary

    This study details the crystal structure of a C(13)H(12)O(4) molecule, revealing a slightly distorted indane ring. Intermolecular hydrogen bonds stabilize the crystal lattice through chain formation.

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    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

    Published on: June 20, 2014

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • The indane ring system is a common motif in organic chemistry.
    • Understanding molecular geometry and intermolecular interactions is crucial for predicting material properties.

    Purpose of the Study:

    • To elucidate the crystal structure of the title molecule, C(13)H(12)O(4).
    • To analyze the specific geometric deviations within the indane ring.
    • To investigate the intermolecular interactions governing crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction analysis.
    • Analysis of atomic coordinates and bond lengths/angles.
    • Identification and characterization of hydrogen bonding networks.

    Main Results:

    • The hydroxy-bearing carbon atom deviates by 0.134(1) Å from the plane of the indane ring.
    • The root-mean-square deviation of the planar atoms is 0.010 Å, indicating near planarity.
    • Molecules form chains along the b-axis via intermolecular O-H⋯O hydrogen bonds.
    • Weak intermolecular C-H⋯O hydrogen bonds further stabilize the crystal structure.

    Conclusions:

    • The crystal structure of C(13)H(12)O(4) exhibits a distorted indane core.
    • Intermolecular hydrogen bonding plays a significant role in the three-dimensional crystal architecture.
    • The identified hydrogen bonding patterns provide insights into the solid-state behavior of this compound.