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Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

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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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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...
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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

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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...
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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...
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Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

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The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Catalyst-controlled Wacker-type oxidation: facile access to functionalized aldehydes.

Zachary K Wickens1, Kacper Skakuj, Bill Morandi

  • 1Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.

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|January 14, 2014
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Summary
This summary is machine-generated.

A novel nitrite-modified Wacker oxidation efficiently converts oxygenated alkenes into aldehydes with high selectivity. This method facilitates the enantioselective synthesis of pharmaceuticals like atomoxetine.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Wacker oxidation is a cornerstone of alkene functionalization.
  • Selective oxidation of oxygenated alkenes remains a synthetic challenge.
  • Development of new catalytic systems is crucial for efficient synthesis.

Purpose of the Study:

  • To develop an aldehyde-selective oxidation of alkenes with allylic/homoallylic oxygen groups.
  • To achieve high yields and selectivity using a modified Wacker oxidation.
  • To explore the utility of this method in synthesizing pharmaceutical agents and understand mechanistic aspects.

Main Methods:

  • Nitrite-modified Wacker oxidation of oxygenated alkenes.
  • Utilizing readily available starting materials.
  • Enantioselective synthesis of atomoxetine.
  • Investigation of functional group influence on the anti-Markovnikov reaction.

Main Results:

  • Achieved up to 88% aldehyde yield and 97% aldehyde selectivity.
  • Demonstrated the method's applicability in the synthesis of the pharmaceutical atomoxetine.
  • Gained preliminary mechanistic insights into the anti-Markovnikov reaction influenced by proximal groups.

Conclusions:

  • Nitrite-modified Wacker oxidation provides an efficient route to aldehydes from oxygenated alkenes.
  • This methodology enables rapid and enantioselective synthesis of valuable compounds.
  • Understanding functional group effects offers avenues for further reaction optimization and mechanistic studies.