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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

Structure and Nomenclature of Epoxides

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...

Preparation of Epoxides

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...

Reactivity of Enols

Reactivity of Enols

Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is governed by factors like...

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

Nitrosation of Enols

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

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Related Experiment Video

Updated: Jun 5, 2026

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Published on: January 8, 2016

4,4'-(Oxydimethyl-ene)dibenzonitrile.

Jie Xiao¹, Hong Zhao

¹Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

A novel organic compound was accidentally synthesized. Its crystal structure reveals a specific dihedral angle and intermolecular hydrogen bonding, forming molecular chains.

Area of Science:

Organic Chemistry
Crystallography

Background:

Accidental synthesis of novel organic compounds can lead to unexpected discoveries.
Understanding molecular interactions is crucial in materials science.

Purpose of the Study:

To characterize a serendipitously synthesized organic compound.
To investigate the crystal structure and intermolecular interactions of the title compound.

Main Methods:

Chemical synthesis.
X-ray diffraction analysis to determine crystal structure.

Main Results:

The compound C(16)H(12)N(2)O was synthesized unexpectedly from 4-(bromo-meth-yl)benzonitrile and penta-erythritol.
The dihedral angle between benzene rings was determined to be 57.39(9)°.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Intermolecular C-H⋯N hydrogen bonds link molecules into chains along the b axis.

Conclusions:

The accidental synthesis yielded a compound with a defined molecular conformation.
The crystal packing is governed by specific hydrogen bonding interactions, influencing the material's structure.