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Cycloalkanes

Cycloalkanes

Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...

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.

Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.

Stability of Substituted Cyclohexanes

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

Cycloaddition Reactions: MO Requirements for Thermal Activation

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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C-H functionalisation of cycloalkanes.

Arghya Banerjee¹, Satavisha Sarkar¹, Bhisma K Patel¹

¹Department of Chemistry, Indian Institute of Technology Guwahati, 781 039, Assam, India. patel@iitg.ernet.in.

Organic & Biomolecular Chemistry

|December 8, 2016

Summary

This review explores recent advances in cycloalkylation, a key method for functionalizing hydrocarbons. It covers both metal-catalyzed and metal-free reactions for creating carbon-carbon and carbon-heteroatom bonds.

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Hydrocarbons are abundant and inexpensive organic compounds, making their selective functionalization highly desirable.
Developing efficient synthetic routes to modify inert hydrocarbon C-H bonds is a significant challenge in chemistry.

Approach:

This review critically examines recent developments in directed and non-directed cycloalkylation reactions.
It encompasses both transition metal-catalyzed and metal-free methodologies.

Key Points:

Cycloalkylation enables the formation of crucial carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds.
Recent advances have expanded the scope of both metal-mediated and metal-free cycloalkylation strategies.
Selective functionalization of C-H bonds in hydrocarbons is addressed.

Conclusions:

The review highlights progress in cycloalkylation for hydrocarbon functionalization.
It underscores the growing importance of both catalytic and metal-free approaches in modern synthesis.