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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.8K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.8K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

3.6K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

3.0K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
3.0K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.4K
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.
Selection Rules: Photochemical Activation
2.4K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.9K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
4.9K

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Related Experiment Video

Updated: Mar 10, 2026

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Visible-Light-Mediated Achmatowicz Rearrangement.

Matthew B Plutschack1, Peter H Seeberger1,2, Kerry Gilmore1

  • 1Department of Biomolecular Systems, Max-Planck Institute of Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.

Organic Letters
|December 13, 2016
PubMed
Summary
This summary is machine-generated.

This study introduces a novel photoredox-catalyzed Achmatowicz reaction using furfuryl alcohol derivatives. It efficiently produces functionalized dihydropyranones with a simple, water-soluble byproduct, simplifying purification.

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Green Chemistry

Background:

  • Visible-light photoredox catalysis offers a sustainable route for chemical synthesis.
  • The Achmatowicz reaction is valuable for creating heterocyclic compounds.
  • Traditional methods often require harsh conditions or complex purification.

Purpose of the Study:

  • To develop the first photoredox-catalyzed Achmatowicz reaction of furfuryl alcohol derivatives.
  • To achieve efficient synthesis of functionalized dihydropyranones.
  • To establish a clean and simplified reaction protocol.

Main Methods:

  • Utilizing visible-light photoredox catalysis.
  • Employing furfuryl alcohol derivatives as substrates.
  • Employing aqueous solutions and various light sources, including sunlight.

Main Results:

  • Successfully synthesized functionalized dihydropyranones.
  • Generated sodium bisulfate (NaHSO4) as the sole, easily separable byproduct.
  • Demonstrated direct Boc-protection of the hemiacetal without column chromatography due to byproduct water solubility.

Conclusions:

  • The developed method provides a robust and efficient pathway for dihydropyranone synthesis.
  • The reaction's simplicity and mild conditions align with green chemistry principles.
  • This photoredox catalysis approach offers a practical alternative for accessing valuable heterocyclic scaffolds.