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Related Concept Videos

Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

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.
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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

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.
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

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Related Experiment Video

Updated: Jun 4, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

An Experimental and Computational Investigation into the Allylboration/Defluorinative Semipinacol Rearrangement

Ty Dudas1, Austin Pounder1, Isabella M Umeris1

  • 1Canadian Centre for Research in Advanced Fluorine Technologies and Department of Chemistry and Biochemistry, University of Lethbridge, 4401 University Drive West, Lethbridge, AB T1K 3M4, Canada.

The Journal of Organic Chemistry
|June 3, 2026
PubMed
Summary

This study introduces a novel cascade reaction using fluoroallyl boronates for simultaneous carbon-carbon bond formation and C-F bond activation. The process yields functionalized carbonyl compounds via a unique defluorinative rearrangement, offering a new synthetic pathway.

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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Organoboron Chemistry

Background:

  • Allylboration reactions are versatile tools in organic synthesis.
  • C-F bond activation remains a significant challenge in synthetic chemistry.
  • Semipinacol rearrangements offer pathways to complex molecular architectures.

Purpose of the Study:

  • To develop a novel cascade reaction for concurrent C-C bond formation and C-F bond activation.
  • To explore the utility of (3-fluoroallyl)boronates in synthetic transformations.
  • To investigate a defluorinative semipinacol rearrangement mechanism.

Main Methods:

  • Utilizing (3-fluoroallyl)boronates in a cascade reaction sequence.
  • Employing a defluorinative semipinacol rearrangement mechanism.
  • Performing computational analysis to understand reaction trends.

Main Results:

  • Achieved concurrent C-C bond formation and C-F bond activation.
  • Generated α-functionalized carbonyl products with high selectivity.
  • Demonstrated tolerance for a variety of carbonyl substrates.
  • Identified electronic factors governing migratory aptitude through computational studies.

Conclusions:

  • The developed cascade reaction provides an efficient route to α-functionalized carbonyl compounds.
  • The study elucidates a novel defluorination-driven skeletal reorganization mechanism.
  • This work expands the synthetic utility of organoboron reagents in C-F bond functionalization.