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Related Concept Videos

Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

6.2K
In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction. 
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
6.2K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

4.0K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
4.0K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

4.2K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
4.2K
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

3.5K
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
3.5K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.7K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.7K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.4K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.4K

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Phytophenol Dimerization Reaction: From Basic Rules to Diastereoselectivity and Beyond.

Shuqin Liu1, Xican Li1, Ban Chen1

  • 1School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Guangzhou Higher Education Mega Center, Waihuang East Road No. 232, Guangzhou 510006, China.

Molecules (Basel, Switzerland)
|August 12, 2022
PubMed
Summary
This summary is machine-generated.

Phytophenol dimerization, a radical coupling reaction crucial for lignin biosynthesis, was studied using DPPH radical initiation. Four rules governing dimerization were identified, explaining product formation and diastereoselectivity in biological systems.

Keywords:
diastereoselectivephenolicphytophenolradical couplingstereoselectivity

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Area of Science:

  • Organic Chemistry
  • Biochemistry
  • Polymer Science

Background:

  • Phytophenol dimerization is a key radical-mediated reaction in lignin biosynthesis.
  • Understanding dimerization mechanisms is vital for controlling product formation in chemical and biological systems.

Purpose of the Study:

  • To elucidate the mechanism and rules governing phytophenol dimerization using a radical initiator.
  • To investigate the role of exocyclic C=C bonds and diastereoselectivity in product formation.
  • To correlate experimental findings with horseradish peroxidase (HRP)-catalyzed reactions and lignin cyclization.

Main Methods:

  • Radical-initiated dimerization of phytophenols in methanol using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical.
  • Product identification via ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC-ESI-Q-TOF-MS/MS).
  • Computational chemistry to analyze reaction pathways and computational chemistry to analyze reaction pathways.

Main Results:

  • Identified various dimer products including biphenols, magnolol, honokiol, and pinoresinols.
  • Defined four basic rules: meta-excluded, C-C bonding domination, ortho-diOH co-activation, and exocyclic C=C involvement.
  • Demonstrated that exocyclic C=C involvement leads to furan-fused dimers with chiral centers and high diastereoselectivity.

Conclusions:

  • The study established fundamental rules for phytophenol dimerization, explaining product outcomes.
  • The findings provide insights into the diastereoselective nature of HRP-catalyzed reactions and lignin cyclization.
  • The established rules can predict product formation in various chemical and biological processes, particularly in oxidase-catalyzed lignin formation.