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Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is activated by...
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

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 strong interaction...
Protecting Groups for Aldehydes and Ketones: Introduction01:23

Protecting Groups for Aldehydes and Ketones: Introduction

Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.
Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

Aldol Condensation with β-Diesters: Knoevenagel Condensation

The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.
Factors Affecting α-Alkylation of Ketones: Choice of Base01:10

Factors Affecting α-Alkylation of Ketones: Choice of Base

α-Alkylation of ketones is achieved in the presence of alkyl halides and a base. The reaction proceeds via the formation of an enolate ion followed by nucleophilic substitution. The choice of base employed is essential as it is the key factor in determining the reaction outcome.
The reaction involving bases like EtO− whose conjugate acid EtOH (pKa = 15.9) is stronger than the ketone (pKa = 19.2) results in an equilibrium mixture with higher ketone concentration. As a consequence, side reactions...
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.

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Updated: Jul 9, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

An efficient and general approach to beta-functionalized ketones.

Jingliang Jiao1, Larry X Nguyen, Dennis R Patterson

  • 1Department of Chemistry, Lehigh University, Bethlehem, PA 18015, USA.

Organic Letters
|March 6, 2007
PubMed
Summary
This summary is machine-generated.

This study introduces a new method for synthesizing beta-functionalized ketones using ceric ammonium nitrate (CAN) and cyclopropyl alcohols. This oxidation reaction offers a straightforward and efficient alternative for creating key organic synthesis intermediates.

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Last Updated: Jul 9, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Oxidation Reactions

Background:

  • Beta-functionalized ketones are valuable building blocks in organic synthesis.
  • Existing methods for their synthesis may involve harsh conditions or multiple steps.

Purpose of the Study:

  • To develop a novel and efficient method for synthesizing beta-functionalized ketones.
  • To explore the oxidation of various anions using ceric ammonium nitrate (CAN) in the presence of cyclopropyl alcohols.

Main Methods:

  • Oxidation of anions (azide, thiocyanate, iodide, bromide) using ceric ammonium nitrate (CAN).
  • Reaction in the presence of substituted cyclopropyl alcohols under mild, neutral conditions.
  • Utilizing readily available reagents and short reaction times.

Main Results:

  • Successful synthesis of beta-functionalized ketones via a novel oxidation pathway.
  • Demonstration of the protocol's efficiency with various substituted cyclopropyl alcohols.
  • Confirmation of advantages including ease of handling and mild reaction conditions.

Conclusions:

  • The developed CAN-mediated oxidation provides a novel and advantageous route to beta-functionalized ketones.
  • This method serves as a valuable alternative for accessing important synthetic intermediates.
  • The protocol's simplicity and efficiency make it attractive for organic synthesis applications.