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Related Concept Videos

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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

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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

2.3K
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.
2.3K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

10.1K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
10.1K
SN2 Reaction: Mechanism02:27

SN2 Reaction: Mechanism

15.2K
The kinetic studies of SN2 reactions suggest an essential feature of its mechanism: it is a single-step process without intermediates. Here, both the nucleophile and the substrate participate in the rate-determining step.
The presence of the more electronegative halogen in the substrate creates a polarized carbon-halide bond. The halide pulls the electron cloud generating an electrophilic center at the carbon atom. Thus, the carbon atom carries a partial positive charge while the halide has a...
15.2K
Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

2.2K
Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...
2.2K
SN2 Reaction: Transition State02:26

SN2 Reaction: Transition State

10.5K
An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...
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Updated: Oct 21, 2025

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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The Chemistry behind ThiC Rearrangement.

Ying-Jie Sun1,2, Liang Cheng1,2

  • 1Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China.

Chembiochem : a European Journal of Chemical Biology
|September 8, 2021
PubMed
Summary

Thiamine (vitamin B1) biosynthesis involves complex steps. This review details the ThiC rearrangement mechanism, enzymes, and genes essential for creating the thiamine pyrimidine moiety.

Keywords:
SAM enzymeThiCnucleosidesrearrangementthiamine

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Enzymology

Background:

  • Thiamine (vitamin B1) is vital for cellular metabolism.
  • Thiamine synthesis involves independent construction of thiazole and pyrimidine rings.
  • The enzymatic mechanisms for thiamine pyrimidine synthesis remain less understood than for the thiazole moiety.

Purpose of the Study:

  • To review recent advancements in understanding the ThiC rearrangement.
  • To elucidate the mechanism, enzymes, and genes involved in thiamine pyrimidine biosynthesis.

Main Methods:

  • Literature review of recent research on ThiC rearrangement.
  • Analysis of mechanistic enzymology studies.
  • Compilation of data on involved genes and enzymes.

Main Results:

  • Detailed summary of the ThiC rearrangement mechanism.
  • Identification and description of key enzymes and genes facilitating the rearrangement.
  • Highlighting the complexity and significance of the thiamine pyrimidine pathway.

Conclusions:

  • The ThiC rearrangement is a critical and complex step in thiamine biosynthesis.
  • Further research into the mechanistic enzymology of ThiC is crucial for a complete understanding of thiamine production.
  • Understanding these pathways can have implications for metabolic engineering and drug development.