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Halogenation of Alkenes02:46

Halogenation of Alkenes

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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.
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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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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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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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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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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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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.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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Interrupting the Nazarov Cyclization with Bromine.

Devon J Schatz1, Yonghoon Kwon1, Thomas W Scully1

  • 1Department of Chemistry, University of Alberta , E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada.

The Journal of Organic Chemistry
|December 17, 2016
PubMed
Summary

This study introduces a new method for creating dibrominated cyclopentenones using an interrupted Nazarov cyclization. The process efficiently installs two bromine atoms at specific positions, yielding a symmetrical product with high diastereoselectivity.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Cyclization Reactions

Background:

  • Nazarov cyclization is a key reaction for forming cyclopentenones.
  • Controlling regioselectivity and stereoselectivity in cyclization reactions remains a challenge.
  • Dibromination of organic scaffolds can lead to versatile synthetic intermediates.

Purpose of the Study:

  • To report a novel method for synthesizing dibrominated cyclopentenones.
  • To investigate the mechanism of bromine installation during an interrupted Nazarov cyclization.
  • To achieve diastereoselective synthesis of dibrominated cyclopentenones.

Main Methods:

  • Interrupted Nazarov cyclization of cyclopentenone precursors.
  • Sequential nucleophilic and electrophilic bromination.
  • Analysis of reaction products for structure and stereochemistry.

Main Results:

  • Successful generation of dibrominated cyclopentenones.
  • Bromine atoms installed at the α and α' positions of the cyclopentenyl scaffold.
  • High diastereoselectivity observed, favoring the symmetrical product.

Conclusions:

  • The interrupted Nazarov cyclization provides an effective route to dibrominated cyclopentenones.
  • The reaction mechanism involves bromination of a 2-oxidocyclopentenyl cation and its enolate.
  • This method offers a diastereoselective approach to valuable synthetic building blocks.