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Related Concept Videos

Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.9K
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...
5.9K
Halogenation of Alkenes02:46

Halogenation of Alkenes

17.2K
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.
17.2K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.3K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.3K
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

2.7K
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
2.7K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

13.9K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
13.9K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

9.1K
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.
9.1K

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Silver Salt-Mediated Allylation Reactions Using Allyl Bromides.

Xiaodong Xiong1, Jonathan Wong1, Ying-Yeung Yeung1

  • 1Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, NT, Hong Kong.

The Journal of Organic Chemistry
|April 16, 2021
PubMed
Summary

A new, efficient method synthesizes allylic amides using allyl bromides and silver triflate. This Ritter-type reaction works under mild conditions, producing diverse allyl-substituted products without needing a base.

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Allylic amides are important synthetic intermediates.
  • Existing methods for allylic amide synthesis can be complex or require harsh conditions.

Purpose of the Study:

  • To develop a facile, efficient, and chemoselective synthesis of allylic amides.
  • To explore the application of this method with various nucleophilic partners.

Main Methods:

  • Utilized allyl bromides as precursors.
  • Activated precursors with silver triflate.
  • Performed a Ritter-type reaction under mild conditions.

Main Results:

  • Successfully synthesized various allylic amides.
  • Demonstrated the reaction's applicability to diverse nucleophilic partners.
  • Achieved product formation in the absence of a base.

Conclusions:

  • A straightforward and efficient synthetic route to allylic amides has been established.
  • The developed protocol offers a versatile approach for generating a wide range of allyl-substituted compounds.
  • The reaction proceeds under mild, base-free conditions, enhancing its practical utility.