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Related Concept Videos

Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

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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
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

3.6K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
3.6K
Radical Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

3.9K
The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy...
3.9K
Halogenation of Alkenes02:46

Halogenation of Alkenes

16.1K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
16.1K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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

2.8K
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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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Two Green Protocols for Halogenative Semipinacol Rearrangement.

Liyan Song1, Yiqin Zhou2, Hanbin Liang2

  • 1Key Laboratory of Biopesticide and Chemical Biology (Ministry of Education), College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou, Fujian 350002, China.

The Journal of Organic Chemistry
|December 8, 2022
PubMed
Summary

This study introduces a safe and green method for semipinacol rearrangement using oxone/halide and Fenton bromide. This approach efficiently generates carbonyl compounds with alpha-quaternary carbon centers under mild conditions.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Semipinacol rearrangement is a key Wagner-Meerwein rearrangement variant.
  • It is crucial for synthesizing natural products and complex molecules with quaternary carbons.

Purpose of the Study:

  • To develop a safe, green, and efficient protocol for halogenative semipinacol rearrangement.
  • To enable the construction of alpha-quaternary carbon centers under mild conditions.

Main Methods:

  • Utilized oxone/halide and Fenton bromide for halogenative semipinacol rearrangement.
  • Employed green in situ generation of reactive halogenating species using oxone or hydrogen peroxide.
  • Conducted reactions at room temperature, insensitive to air and moisture.

Main Results:

  • Successfully achieved semipinacol rearrangement to yield carbonyl compounds with alpha-quaternary carbon centers.
  • Demonstrated a green approach with non-toxic byproducts like potassium sulfate or water.
  • The protocol is operationally simple, requiring no special equipment.

Conclusions:

  • The developed protocol offers a safe, green, and practical alternative for semipinacol rearrangement.
  • This method facilitates the synthesis of complex organic molecules, particularly natural products.
  • The operational simplicity and mild conditions make it broadly applicable in synthetic chemistry.