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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.5K
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.
2.5K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.1K
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
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.9K
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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Sharpless Epoxidation02:57

Sharpless Epoxidation

4.9K
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...
4.9K

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Related Experiment Video

Updated: Dec 29, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

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Deracemization Enabled by Visible-Light Photocatalysis.

Qinglong Shi1, Juntao Ye1

  • 1Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, P. R. China.

Angewandte Chemie (International Ed. in English)
|February 8, 2020
PubMed
Summary
This summary is machine-generated.

Visible-light photocatalysis offers a promising route for deracemization, converting racemic mixtures into single enantiomers. This method selectively transforms chiral molecules like allenes, cyclopropylquinolones, and cyclic ureas.

Keywords:
deracemizationenantioselectivityenergy transferphotocatalysisvisible light

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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Asymmetric Synthesis

Background:

  • Deracemization, the conversion of racemic mixtures to single enantiomers, is highly desirable but challenging.
  • Chiral molecules are crucial in pharmaceuticals and materials science.

Purpose of the Study:

  • To explore visible-light photocatalysis as a method for selective deracemization.
  • To demonstrate the application of photocatalysis in deracemizing axially and centrally chiral compounds.

Main Methods:

  • Utilizing visible-light photocatalysis to initiate deracemization reactions.
  • Investigating energy transfer pathways.
  • Exploring sequences of electron, proton, and hydrogen-atom transfer.

Main Results:

  • Successful selective deracemization of axially chiral allenes.
  • Demonstrated deracemization of cyclopropylquinolones and cyclic ureas with central chirality.
  • Photocatalysis proved effective through various proposed mechanisms.

Conclusions:

  • Visible-light photocatalysis is a viable and effective strategy for the selective deracemization of diverse chiral molecules.
  • The methodology offers a powerful tool for accessing enantiomerically pure compounds.