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Related Concept Videos

Halogenation of Alkenes02:46

Halogenation of Alkenes

18.4K
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.
18.4K
Structure and Bonding of Alkenes02:47

Structure and Bonding of Alkenes

20.2K
Olefins, which are unsaturated hydrocarbons containing one or more carbon–carbon double bonds, are broadly divided into alkenes and cycloalkenes. The general chemical formula of an alkene is CnH2n.
Doubly bonded carbons are sp2 hybridized and have a trigonal planar geometry. The double bond is composed of a σ bond formed by the overlap of hybrid orbitals and a π bond produced by the lateral overlap of unhybridized 2p orbitals on both the carbons. Each carbon atom is...
20.2K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

3.4K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
3.4K
Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

10.1K
The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...
10.1K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

12.1K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
12.1K
Isomerism in Alkenes02:01

Isomerism in Alkenes

14.7K
Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
14.7K

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Intermolecular 1,2-difunctionalization of alkenes.

Yuanrui Wang1,2, Zhi-Peng Bao1,3, Xu-Dong Mao1,3

  • 1Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 116023 Dalian, Liaoning, China. xwu2020@dicp.ac.cn.

Chemical Society Reviews
|September 22, 2025
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Summary

Directly adding two functional groups to alkenes (olefins) increases molecular complexity. This review covers recent advances in 1,2-difunctionalization reactions of olefins, focusing on mechanisms and functional group types.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Alkenes possess a carbon-carbon double bond, enabling diverse chemical transformations.
  • Direct difunctionalization of olefins rapidly increases molecular complexity by introducing two functional groups simultaneously.
  • This process enhances the application value of organic compounds.

Purpose of the Study:

  • To review the latest advancements in the 1,2-difunctionalization of olefins over the past five years.
  • To categorize the reaction mechanisms and types of functional groups involved in olefin difunctionalization.
  • To provide a comprehensive overview of this synthetic strategy, excluding cyclization reactions.

Main Methods:

  • Exploration of transition metal-mediated addition and coupling reactions.
  • Investigation of radical addition pathways to olefins.
  • Analysis of single-electron transfer strategies involving radical intermediates.

Main Results:

  • Significant progress has been made in achieving previously challenging olefin difunctionalization reactions.
  • Three primary reaction modes for olefin difunctionalization have been identified: transition metal-catalyzed, radical-mediated, and single-electron transfer pathways.
  • The review classifies various functional group introductions and reaction mechanisms.

Conclusions:

  • Innovations in synthetic chemistry have enabled efficient 1,2-difunctionalization of olefins.
  • Understanding the mechanisms and functional group scope is crucial for advancing synthetic strategies.
  • This review serves as a valuable resource for researchers in organic and synthetic chemistry.