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Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

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Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
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Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

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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...
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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
5.7K
Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction01:09

Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction

6.0K
Wolff–Kishner reduction involves converting aldehydes and ketones to alkanes using hydrazine and a base. The reaction converts a carbonyl group to a methylene group. The method was independently discovered by N. Kishner in 1911 and L. Wolff in 1912. The reduction is carried out in high-boiling solvents such as ethylene glycol and diethylene glycol because heat is required to deprotonate the N–H proton in one of the reaction steps.                                       ...
6.0K
Oxidation of Alcohols02:37

Oxidation of Alcohols

18.0K
In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
18.0K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Direct Access to β-Fluorinated Aldehydes by Nitrite-Modified Wacker Oxidation.

Crystal K Chu1, Daniel T Ziegler1, Brian Carr1

  • 1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, 91125, USA.

Angewandte Chemie (International Ed. in English)
|May 27, 2016
PubMed
Summary

This study introduces a novel nitrite-catalyzed Wacker-type oxidation for allylic fluorides, directly yielding valuable β-fluorinated aldehydes. This efficient method offers a versatile route to diverse fluorinated building blocks.

Keywords:
aldehydesfluorineoxidationpalladiumregioselectivity

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Area of Science:

  • Organic Chemistry
  • Fluorine Chemistry
  • Catalysis

Background:

  • Wacker-type oxidation is a crucial transformation in organic synthesis.
  • Direct functionalization of allylic fluorides remains challenging.
  • Access to fluorinated aldehydes and building blocks is highly desirable.

Purpose of the Study:

  • To develop a novel aldehyde-selective Wacker-type oxidation of allylic fluorides.
  • To establish a direct synthetic route to β-fluorinated aldehydes.
  • To explore the utility of the generated aldehydes as versatile intermediates.

Main Methods:

  • Utilized a nitrite catalyst for Wacker-type oxidation.
  • Employed a range of allylic fluorides with diverse functional groups.
  • Investigated preliminary mechanistic aspects, including inductive effects.

Main Results:

  • Achieved aldehyde-selective oxidation of allylic fluorides with high yield.
  • Demonstrated very high regioselectivity in the transformation.
  • Showcased the utility of unpurified aldehyde products for synthesizing various fluorinated building blocks.

Conclusions:

  • Developed an efficient and direct method for synthesizing β-fluorinated aldehydes from allylic fluorides.
  • The methodology provides access to a diverse range of fluorinated intermediates.
  • Inductive effects significantly influence the reaction's rate and regioselectivity.