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Related Concept Videos

Mass Spectrometry: Molecular Fragmentation Overview01:20

Mass Spectrometry: Molecular Fragmentation Overview

The ionization of a molecule into a molecular ion inside the mass spectrometer causes instability in the molecule's structure due to the loss of an electron. This eventually leads to the fragmentation or breaking of some bonds in the molecule. The fragmentation occurs predominantly at specific bonds to yield relatively stable fragments.
One type of fragmentation pattern is the cleavage of a single bond in the molecular ion. The cleavage leads to a radical and a cation. The cleavage can occur at...
Mass Spectrometry: Cycloalkene Fragmentation00:54

Mass Spectrometry: Cycloalkene Fragmentation

The molecular ions of cycloalkenes undergo fragmentation via a retro-Diels–Alder reaction.
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Ethers to Alkyl Halides: Acidic Cleavage02:18

Ethers to Alkyl Halides: Acidic Cleavage

Ethers are generally unreactive and unsuitable for direct nucleophilic substitution reactions since the alkoxy groups are strong bases and, therefore, poor leaving groups. However, ethers readily undergo acidic-cleavage reactions. Ethers can be converted to alkyl halides when heated with strong acids such as HBr and HI in a sequence of two substitution reactions.
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...

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Workflow and Tools for Crystallographic Fragment Screening at the Helmholtz-Zentrum Berlin
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A fragment based approach toward thia[n]helicenes.

Deepali Waghray1, Wim Dehaen

  • 1Molecular Design and Synthesis, Department of Chemistry, KU Leuven , Celestijnenlaan 200F, 3001 Leuven, Belgium.

Organic Letters
|June 6, 2013
PubMed
Summary

This study reports the synthesis of various thiahelicenes using efficient palladium-catalyzed coupling reactions and visible light photocyclization. The modular method allows for the creation of diverse thiahelicene structures, regardless of backbone length.

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Published on: August 1, 2018

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Helicenes are chiral aromatic compounds with unique photophysical properties.
  • Thiahelicenes, incorporating sulfur atoms into the helical backbone, offer modified electronic and structural characteristics.
  • Developing efficient synthetic routes for diverse thiahelicene structures is crucial for exploring their potential applications.

Purpose of the Study:

  • To report the synthesis of [9]- and [11]thiahelicenes and their lower homologues ([5]-, [6]-, [7]thiahelicenes).
  • To establish a modular synthetic methodology for thiahelicenes.
  • To explore the use of palladium-catalyzed coupling and photocyclization reactions in thiahelicene synthesis.

Main Methods:

  • Palladium-catalyzed coupling reactions, including Stille coupling.
  • Selective mono-cross-coupling of triorganoindium derivatives with N-methyl-3,4-dibromomaleimide.
  • Oxidative photocyclization of conjugated precursors using visible light.

Main Results:

  • Successful synthesis of [5]-, [6]-, [7]-, [9]-, and [11]thiahelicenes.
  • Demonstration of a modular synthetic approach applicable to various thiahelicene lengths.
  • Efficient preparation of conjugated precursors via Stille coupling.

Conclusions:

  • A versatile and modular synthetic strategy for thiahelicenes has been developed.
  • The methodology is independent of the helical backbone length, enabling access to a wide range of thiahelicenes.
  • This work provides a foundation for further investigation into the properties and applications of thiahelicenes.