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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Directing Effect of Substituents: ortho–para-Directing Groups01:14

Directing Effect of Substituents: ortho–para-Directing Groups

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Ortho–para directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para to the substituent. All electron-donating groups are considered ortho–para directors. They donate electrons to the ring and make the ring more electron-rich. The ring is therefore susceptible to the addition of electrophiles. Substituents such as amino, hydroxy, or alkoxy, containing lone pairs on the atom adjacent to the ring, donate...
8.3K
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

5.7K
Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
5.7K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

6.6K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
6.6K
Propagation of Waves01:07

Propagation of Waves

2.9K
When a wave propagates from one medium to another, part of it may get reflected in the first medium, and part of it may get transmitted to the second medium. In such a case, the interface of the two mediums can be considered as a boundary that is neither fixed nor free.
Consider a scenario where a wave propagates from a string of low linear mass density to a string of high linear mass density. In such a case, the reflected wave is out of phase with respect to the incident wave, however the...
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Propagation of Action Potentials01:23

Propagation of Action Potentials

9.1K
The propagation of an action potential refers to the process by which a nerve impulse, or "action potential," travels along a neuron.
Neurons (nerve cells) have a resting membrane potential, with a slightly negative charge inside compared to outside. This is maintained by ion channels, such as sodium (Na+) and potassium (K+) channels, which control the flow of ions. When a stimulus, like a touch or a signal from another neuron, triggers the neuron, sodium channels open, allowing sodium ions to...
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Synthesis of Programmable Main-chain Liquid-crystalline Elastomers Using a Two-stage Thiol-acrylate Reaction
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Self-Propagated para-Fluoro-Thiol Reaction.

Federica Cavalli1, Fabian R Bloesser2, Christopher Barner-Kowollik2,3,4

  • 1Soft Matter Synthesis Laboratory, Institut für Biologische Grenzflächen, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344, Eggenstein-Leopoldshafen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 14, 2019
PubMed
Summary

This study presents a protecting-group-free method for the para-fluoro-thiol reaction (PFTR), utilizing fluoride ions as a base. The reaction is self-propagating and requires minimal base, enabling efficient thiol functionalization.

Keywords:
basefluorinepara-fluoro thiolself-sustainedsynthetic methods

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • The para-fluoro-thiol reaction (PFTR) is a powerful tool for thiol functionalization.
  • Traditional PFTR often requires high concentrations of base, limiting its applicability.

Purpose of the Study:

  • To develop a protecting-group-free concept for the PFTR.
  • To enable the PFTR to proceed with minimal or no base.

Main Methods:

  • Utilizing a source of fluoride ions as a base.
  • Employing a self-propagating reaction mechanism.
  • Optimizing solvent-thiol combinations.

Main Results:

  • Achieved quantitative conversion in the PFTR without protecting groups.
  • Demonstrated self-propagation with under-stoichiometric amounts of base.
  • Showcased base-free PFTR under optimized conditions.

Conclusions:

  • The developed protecting-group-free concept significantly simplifies the PFTR.
  • Minimal base requirement and self-propagation offer a more efficient and versatile synthetic route.
  • This advancement broadens the scope and accessibility of thiol functionalization via PFTR.