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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

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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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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
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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.
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Reductive dimerization of benzothiazolium salts.

Aijaz Shaikh1, Satyajit Sahoo1, Seth R Marder2,3

  • 1Department of Industrial and Engineering Chemistry, Institute of Chemical Technology-Indian Oil Odisha Campus, IIT Kharagpur Extension Center, Bhubaneswar, Odisha 751013, India. sk.mohapatra@iocb.ictmumbai.edu.in.

Organic & Biomolecular Chemistry
|February 20, 2024
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Summary

Reduction of benzothiazolium salts yields diverse dimeric products, including bibenzothiazoles and benzothiazino-benzothiazines. These compounds exhibit distinct electrochemical properties and reactivity, with bibenzothiazoles readily oxidizing.

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Area of Science:

  • Organic Chemistry
  • Heterocyclic Chemistry
  • Materials Science

Background:

  • Benzothiazolium salts are versatile precursors in organic synthesis.
  • The reduction of heterocyclic compounds can lead to various complex structures.
  • Understanding the reactivity of reduced heterocycles is crucial for developing new materials and synthetic methodologies.

Purpose of the Study:

  • To investigate the reduction products of 2-substituted 3-methylbenzothiazolium salts.
  • To explore the structural diversity and chemical properties of the resulting dimeric compounds.
  • To study the electrochemical behavior and reactivity of the synthesized bibenzothiazoles and benzothiazino-benzothiazines.

Main Methods:

  • Reduction of 2-substituted 3-methylbenzothiazolium salts using sodium amalgam (Na-Hg).
  • Structural characterization of reaction products using single-crystal X-ray diffraction.
  • Electrochemical studies (cyclic voltammetry) and reactivity assessments with various oxidants.

Main Results:

  • Two distinct types of dimeric products were obtained: 2,2'-bibenzo[d]thiazoles and cis-[1,4]benzothiazino[3,2-b][1,4]benzothiazines, depending on the 2-substituent.
  • Disulfide derivatives were formed from bibenzo[d]thiazoles in the presence of molecular oxygen.
  • 2,2'-bibenzo[d]thiazoles showed oxidation potentials comparable to ferrocene and were reversible to benzothiazolium cations with mild oxidants.
  • Benzothiazino-benzothiazines exhibited electrochemical stability within the tested solvent window.

Conclusions:

  • The reduction of 2-substituted 3-methylbenzothiazolium salts offers a pathway to structurally diverse dimeric heterocyclic compounds.
  • The nature of the 2-substituent dictates the formation of either bibenzothiazole or benzothiazino-benzothiazine frameworks.
  • The distinct electrochemical properties of these dimeric compounds suggest potential applications in redox-active materials and synthetic chemistry.