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Related Concept Videos

Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

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Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
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α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

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α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
3.4K
Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

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Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.2K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.2K
Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation00:43

Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation

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As shown in Figure 1, under acidic conditions, the β-hydroxy ketone undergoes dehydration via an E1 elimination reaction to form an enone.
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Amidation of Enones via Beckmann Rearrangement.

Saumya Verma1, Vikram Singh2, Jawahar L Jat1

  • 1Department of Chemistry, Babasaheb Bhimrao Ambedkar University (A Central University) Vidya Vihar, Raebareli Road, Lucknow 226025, Uttar Pradesh, India.

The Journal of Organic Chemistry
|May 27, 2024
PubMed
Summary
This summary is machine-generated.

This study presents a new method for synthesizing unsaturated amides directly from enones. The novel approach overcomes previous limitations, enabling efficient amide preparation.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Background:

  • The Beckmann reaction is a highly atom-economical route to amides from ketones.
  • Applying the Beckmann reaction to enones for α,β-unsaturated amide synthesis is challenging due to competing reactivities and harsh conditions for oxime formation.

Purpose of the Study:

  • To develop the first chemoselective method for directly converting enones into α,β-unsaturated amides.
  • To establish milder reaction conditions for this transformation.

Main Methods:

  • Utilized *N*-Boc-*O*-tosylhydroxylamine as a key reagent.
  • Developed a direct conversion protocol for enones.

Main Results:

  • Achieved the first chemoselective direct conversion of enones to α,β-unsaturated amides.
  • Demonstrated the efficacy of *N*-Boc-*O*-tosylhydroxylamine in this transformation.

Conclusions:

  • The developed method offers a significant advancement for synthesizing α,β-unsaturated amides.
  • This approach overcomes limitations associated with traditional Beckmann reaction conditions for enone substrates.