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Related Concept Videos

Directing and Steric Effects in Disubstituted Benzene Derivatives01:18

Directing and Steric Effects in Disubstituted Benzene Derivatives

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When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the...
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Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
5.9K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
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Protonation Effects on the Benzoxazine Formation Pathways and Products Distribution.

Francisco W M Ribeiro1,2, Isaac Omari1, J Scott McIndoe1

  • 1Department of Chemistry, University of Victoria, P. O. Box 3065, Victoria, BC V8W 3V6, Canada.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|June 11, 2024
PubMed
Summary

Acidic conditions influence benzoxazine synthesis by promoting specific intermediates. While acid aids some steps, it doesn't facilitate the final cyclization for benzoxazine (Bz) formation.

Keywords:
Acid CatalysisBenzoxazinesMass SpectrometryPolybenzoxazinesReaction Mechanism

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Area of Science:

  • Organic Chemistry
  • Reaction Mechanism Studies

Background:

  • Benzoxazines are heterocyclic compounds with diverse applications.
  • Understanding their synthesis pathways is crucial for optimizing production.
  • Acidic media effects on benzoxazine formation are not fully elucidated.

Purpose of the Study:

  • To investigate the impact of acidic media on 3,4-dihydro-2H-3-phenyl-1,3-benzoxazine (Bz) formation.
  • To differentiate reaction pathways and intermediates in the presence and absence of acid.
  • To identify optimal conditions for benzoxazine synthesis.

Main Methods:

  • Real-time mass spectrometry (PSI-ESI-MS) coupled with tandem mass spectrometry.
  • Infrared multiple photon dissociation (IRMPD) for species differentiation.
  • Comparative analysis of reaction pathways under acidic and neutral conditions.

Main Results:

  • Formic acid promotes aniline and phenol condensation products (IC and IIC) by protecting the amino group and increasing formaldehyde electrophilicity.
  • Acidic conditions provide a more efficient potential energy landscape for certain reaction steps.
  • The final cyclization step to form benzoxazines is not mediated by the protonation route intermediate (ROP Bz).

Conclusions:

  • Acidic conditions significantly alter benzoxazine synthesis pathways.
  • Specific intermediates are favored under acidic catalysis.
  • The findings provide insights for developing optimized benzoxazine synthesis protocols.