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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,...
Electron Affinity03:07

Electron Affinity

The electron affinity (EA) is the energy change for adding an electron to a gaseous atom to form an anion (negative ion).
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...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization

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Related Experiment Video

Updated: May 26, 2026

Photoelectron Imaging of Anions Illustrated by 310 Nm Detachment of F&#8722;
06:53

Photoelectron Imaging of Anions Illustrated by 310 Nm Detachment of F−

Published on: July 27, 2018

Dissociative electron attachment to triflates.

Sylwia Ptasińska1, David Gschliesser, Peter Bartl

  • 1Radiation Laboratory and Department of Physics, University of Notre Dame, Notre Dame, Indiana 46556, USA. sptasins@nd.edu

The Journal of Chemical Physics
|December 14, 2011
PubMed
Summary
This summary is machine-generated.

Dissociative electron attachment to triflates reveals distinct fragmentation pathways for alkyl and aryl molecules. Understanding these electron-induced bond scissions is crucial for photoacid generator applications in lithography.

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Published on: July 28, 2018

Area of Science:

  • Physical Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Triflates are model molecules for nonionic photoacid generators used in advanced lithography.
  • Understanding their fragmentation under electron impact is key to optimizing lithographic processes.

Purpose of the Study:

  • To investigate the gas-phase dissociative electron attachment pathways of simple alkyl and aryl triflates.
  • To identify major dissociation channels and anion formation under electron impact below 10 eV.

Main Methods:

  • Utilized crossed electron-molecular beam mass spectrometry.
  • Analyzed fragmentation patterns resulting from electron impact on triflate molecules.

Main Results:

  • Identified major dissociation channels involving C-O, S-O, and C-S bond scissions, yielding triflate (OTf(-)), triflyl (Tf(-)), and sulfonate (RSO(3)(-)) anions.
  • Observed lower electron energies for C-O bond cleavage in alkyl triflates compared to aryl triflates.
  • Noted that S-O bond cleavage in aryl triflates occurred at similar electron energies as C-O bond cleavage, unlike in alkyl triflates.

Conclusions:

  • The study elucidates the specific fragmentation mechanisms of alkyl and aryl triflates under electron attachment.
  • Findings provide insights into the stability and reactivity of these molecules, relevant for photoacid generator design in lithography.