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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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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.
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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.
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Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.

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Related Experiment Video

Updated: May 31, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Ethane-1,2-diyl bis-(benzene-dithio-ate).

Daisuke Abe, Yuji Sasanuma, Hiroyasu Sato

    Acta Crystallographica. Section E, Structure Reports Online
    |July 15, 2011
    PubMed
    Summary

    This study details the crystal structure of C(16)H(14)S(4), revealing a specific gauche(+)-trans-gauche(-) conformation. The research also highlights the dihedral angle between the S-C=S plane and the phenyl ring, along with observed intermolecular C-H⋯π interactions.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Supramolecular Chemistry

    Background:

    • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
    • Sulfur-containing organic compounds exhibit diverse structural motifs and intermolecular interactions.
    • Crystal structure analysis provides precise atomic-level details of molecular conformation and packing.

    Purpose of the Study:

    • To elucidate the detailed crystal structure of the title compound, C(16)H(14)S(4).
    • To characterize the conformational preferences within the S-CH(2)-CH(2)-S linkage.
    • To investigate the spatial relationship between the S-C=S plane and the phenyl ring, and identify any significant intermolecular interactions.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular structure.

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  • Analysis of bond lengths, bond angles, and dihedral angles provided conformational information.
  • Identification of intermolecular interactions, such as C-H⋯π interactions, was performed.

    • Main Results:

    • The C(16)H(14)S(4) molecule was found to reside on an inversion center within the crystal lattice.
    • A gauche(+)-trans-gauche(-) conformation was observed in the S-CH(2)-CH(2)-S bond sequence.
    • A dihedral angle of 30.63(17)° was measured between the S-C=S plane and the phenyl ring.
    • Evidence of an intermolecular C-H⋯π interaction was identified.

    Conclusions:

    • The crystal structure of C(16)H(14)S(4) reveals a defined molecular conformation and packing arrangement.
    • The observed gauche(+)-trans-gauche(-) conformation and dihedral angle provide insights into the molecule's preferred spatial orientation.
    • The presence of intermolecular C-H⋯π interactions suggests potential roles in crystal packing and molecular recognition.