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Related Concept Videos

Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Electrodeposition01:08

Electrodeposition

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Electrodeposition is a technique used to separate an analyte from interferents by electrochemical processes. Here, the analyte is a metal ion that can be deposited on an electrode immersed in the sample solution. The electrochemical setup consists of an anode and a cathode. When an electric current is applied to the setup, oxidation occurs at the anode. At the cathode, which consists of a large metal surface, metal ions undergo reduction and deposit onto the surface.
Electrodeposition can...
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Controlled-Potential Coulometry: Electrolytic Methods01:17

Controlled-Potential Coulometry: Electrolytic Methods

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Controlled-potential coulometry, also known as potentiostatic coulometry, employs a three-electrode system in which the working electrode's potential is precisely regulated using a potentiostat. Platinum working electrodes are utilized for positive potentials, while mercury pool electrodes are favored for extremely negative potentials. The platinum counter electrode is separated from the analyte using a membrane or salt bridge to avoid interference in the analysis.
The chosen potential...
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Sharpless Epoxidation02:57

Sharpless Epoxidation

4.4K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.0K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction
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Chemoselective Electrosynthesis Using Rapid Alternating Polarity.

Yu Kawamata1, Kyohei Hayashi1, Ethan Carlson1

  • 1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society
|October 1, 2021
PubMed
Summary
This summary is machine-generated.

Chemoselective reduction of carbonyl compounds is achieved using rapid alternating polarity (rAP) electrolysis. This novel electrochemical method offers precise control, outperforming traditional direct current electrolysis and chemical reagents in complex organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Synthetic Methodology

Background:

  • Chemoselectivity in organic synthesis traditionally relies on tunable reagents or protecting groups.
  • Electrochemical methods offer redox control but struggle with multiple redox-active sites.
  • Direct current (DC) electrolysis is standard, while alternating current (AC) effects are underexplored in preparative synthesis.

Purpose of the Study:

  • To develop a novel electrochemical approach for precise chemoselective reduction of carbonyl compounds.
  • To demonstrate the strategic exploitation of alternating current (AC) in complex organic synthesis.
  • To showcase the utility of rapid alternating polarity (rAP) in overcoming synthetic challenges.

Main Methods:

  • Employing a square waveform to deliver rapid alternating polarity (rAP) electric current.
  • Investigating the chemoselective reduction of carbonyl compounds.
  • Comparing rAP electrolysis with direct current (DC) electrolysis and chemical reagents.

Main Results:

  • Rapid alternating polarity (rAP) electrolysis enables controlled chemoselective reduction of carbonyl compounds.
  • The observed reactivity with rAP cannot be replicated using DC electrolysis or conventional chemical reagents.
  • Demonstrated synthetic utility in chiral auxiliary removal and PROTAC synthesis.

Conclusions:

  • Rapid alternating polarity (rAP) electrolysis is a powerful new tool for achieving chemoselectivity in organic synthesis.
  • This method provides unique reactivity and control, expanding the scope of electrosynthesis.
  • rAP electrolysis offers significant advantages for both classical synthetic problems and modern medicinal chemistry applications.