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Related Concept Videos

π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

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An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

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The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...
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Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

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Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
2.7K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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

2.4K
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.
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Electro-oxidative Intermolecular Allylic C(sp3)-H Aminations.

Yulei Wang1, Zhipeng Lin1, João C A Oliveira1

  • 1Institut für Organische und Biomolekulare Chemie and Wöhler Research Institute for Sustainable Chemistry (WISCh), Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany.

The Journal of Organic Chemistry
|June 2, 2021
PubMed
Summary

This study introduces an electrochemical method for creating nitrogen-containing molecules directly from C-H bonds. This metal- and chemical oxidant-free process offers a greener alternative for synthesizing valuable organic compounds.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Sustainable Synthesis

Background:

  • Oxidative nitrogenation of C(sp3)-H bonds is key for synthesizing nitrogen-containing molecules.
  • Traditional methods often require sacrificial chemical oxidants, posing environmental concerns.

Purpose of the Study:

  • To develop a metal- and chemical oxidant-free method for oxidative intermolecular allylic C(sp3)-H amination.
  • To utilize electrochemistry for a more sustainable synthetic route.

Main Methods:

  • Electrochemical oxidative intermolecular allylic C(sp3)-H amination.
  • Employing an undivided cell powered by electric current.
  • Metal- and chemical oxidant-free reaction conditions.

Main Results:

  • Efficient cross-dehydrogenative amination achieved.
  • Broad substrate scope demonstrated.
  • Molecular hydrogen (H2) identified as the sole byproduct, indicating a clean process.

Conclusions:

  • Electrochemical oxidation provides a direct and efficient pathway for C(sp3)-H amination.
  • This method avoids the need for harsh oxidants and metal catalysts.
  • The developed protocol offers a sustainable and scalable approach to nitrogen-containing compounds.