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Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

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In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
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Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Aromatic Compounds: Overview01:25

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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday...
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Aromatic Hydrocarbon Anions: Structural Overview01:18

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Reactivity of Enols

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Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is...
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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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The aromatic ene reaction.

Dawen Niu1, Thomas R Hoye1

  • 1Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.

Nature Chemistry
|December 19, 2013
PubMed
Summary

This study demonstrates efficient aromatic ene reactions using aryne intermediates to create complex dearomatized isotoluenes. The novel cascade reaction offers a powerful, single-pot method for synthesizing valuable chemical structures.

Area of Science:

  • Organic Chemistry
  • Pericyclic Reactions
  • Synthetic Methodology

Background:

  • The ene reaction is a fundamental pericyclic process involving an alkene (ene donor) and an unsaturated species (enophile).
  • Aromatic ene reactions, where the alkene is part of an aromatic ring, are rare and typically low-yielding.
  • Aryne intermediates are highly reactive species utilized in various synthetic transformations.

Purpose of the Study:

  • To develop efficient methods for aromatic ene reactions.
  • To explore the synthesis of dearomatized isotoluenes via aromatic ene reactions.
  • To establish a novel cascade reaction for complex molecule synthesis.

Main Methods:

  • Computational studies to identify favorable structural features for aromatic ene reactions.

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  • Hexadehydro-Diels-Alder reaction for in situ aryne generation.
  • Intramolecular aromatic ene reaction followed by a bimolecular Alder ene reaction.

    • Main Results:

    • Efficient aromatic ene reactions were achieved using thermally generated aryne intermediates.
    • Dearomatized isotoluenes were synthesized from m-alkylarene substituents.
    • A three-step cascade reaction (hexadehydro-Diels-Alder, intramolecular aromatic ene, Alder ene) was successfully implemented in a single pot.
    • The cascade reaction demonstrated considerable scope and efficiency, producing structurally complex products.

    Conclusions:

    • This work significantly advances the field of aromatic ene reactions by providing an efficient and versatile synthetic route.
    • The developed cascade reaction offers a powerful tool for constructing complex molecular architectures in a reagent- and by-product-free manner.
    • The findings open new avenues for the synthesis and application of dearomatized isotoluenes and related reactive intermediates.