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Halogenation of Alkenes

Halogenation of Alkenes

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.

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

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 confirmed through isotopic...

Reactions at the Benzylic Position: Halogenation

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.

Preparation of Alkynes: Dehydrohalogenation

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

Benzene to Phenol via Cumene: Hock Process

Benzene to Phenol via Cumene: Hock Process

The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene hydroperoxide...

Multiple Halogenation of Methyl Ketones: Haloform Reaction

Multiple Halogenation of Methyl Ketones: Haloform Reaction

A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic acyl substitution.

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Published on: September 18, 2016

Synthesis of Functionalized [5]-Cyclo-m-phenylenes Enabled by Controlled Multihalogenation Using a Carborane

Kohtaro Sugimoto¹, Koji Hirano^1,2, Yuji Nishii^1,2,3

¹Department of Applied Chemistry, Graduate School of Engineering, The University of Osaka, Suita, Osaka 565-0871, Japan.

Organic Letters

|May 18, 2026

Summary

Researchers synthesized novel functionalized [5]carbomethoxy[5]ane (CMP) derivatives with unique substitution patterns. This work provides versatile synthetic routes for complex CMP compounds and their downstream applications.

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Area of Science:

Organic Chemistry
Materials Science

Background:

[5]Carbomethoxy[5]ane (CMP) derivatives are important in various chemical applications.
Developing efficient synthetic routes for CMP derivatives with unconventional substitution patterns is crucial.

Purpose of the Study:

To report the synthesis of functionalized [5]CMP derivatives with unconventional substitution patterns.
To demonstrate versatile derivatization strategies for CMP compounds.

Main Methods:

Controlled multiple bromination using a Carborane-SMe catalyst.
Cyanation and alkynylation for coupling reactions.
Benzylic bromination and nucleophilic substitution for functionalization.

Main Results:

Key intermediate 2 was synthesized in near-quantitative yield.
Diverse functional groups were introduced via nucleophilic substitution at the benzylic position.
Demethylation was achieved through decarboxylation of the corresponding carboxylic acid.

Conclusions:

The methyl substituent of Me5-[5]CMP is a versatile handle for downstream derivatization.
Novel functionalized [5]CMP derivatives with unconventional substitution patterns were successfully synthesized.
The developed methods offer broad applicability for creating complex CMP structures.