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Related Concept Videos

Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[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.
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.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.

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Related Experiment Video

Updated: Jun 1, 2026

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

1-Decyl-indoline-2,3-dione.

Khalil Mamari, Hafid Zouihri, El Mokhtar Essassi

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

    This study details the molecular structure of N-alkyl isatin, revealing a nearly planar isatin core. The decyl chain attached exhibits a fully extended, antiperiplanar conformation, important for understanding molecular packing in related compounds.

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    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Molecular Structure Analysis

    Background:

    • Isatin derivatives are important scaffolds in medicinal chemistry.
    • Understanding the solid-state structure of N-alkyl isatins is crucial for structure-activity relationship studies.

    Purpose of the Study:

    • To elucidate the three-dimensional molecular structure of N-alkyl isatin (C18H25NO2).
    • To determine the conformation of the isatin core and the alkyl substituent.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed.
    • Analysis of bond lengths, bond angles, and torsion angles was performed.

    Main Results:

    • The isatin moiety was found to be nearly planar, with a root-mean-square deviation of 0.03 Å.
    • The decyl substituent adopted a fully extended, all-antiperiplanar conformation.

    Conclusions:

    • The determined structure provides a precise model for N-alkyl isatin derivatives.
    • The planar isatin core and extended alkyl chain influence crystal packing and intermolecular interactions.