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Related Concept Videos

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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Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

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Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
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Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

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Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
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Preparation of Diols and Pinacol Rearrangement01:57

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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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RHAT-Enabled Deoxyfunctionalization of Cyclic Acetals Derived from Vicinal Diols.

Zheng Wang1, Huiying Liu1, Tiantian Liu1

  • 1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, China.

Chemistry, an Asian Journal
|May 29, 2025
PubMed
Summary

This study presents a new radical deoxygenative strategy to functionalize cyclic acetals from diols. The method efficiently synthesizes deconjugated alkenes using visible-light-driven conditions.

Keywords:
Alkene synthesisCyclic acetalsDeconjugated additionDeoxyfunctionalizationHydrogen atom transfer

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Selective activation of strong carbon-oxygen (C-O) bonds in diols is challenging due to high bond energies.
  • Existing methods for diol functionalization often lack regioselectivity or require harsh conditions.

Purpose of the Study:

  • To develop a regioselective radical deoxygenative strategy for functionalizing cyclic acetals derived from vicinal diols.
  • To synthesize deconjugated alkenes under mild, visible-light-driven conditions.

Main Methods:

  • Utilized a visible-light-driven radical deoxygenative approach.
  • Employed cyclic acetals derived from vicinal diols and various alkynes as substrates.
  • Conducted mechanistic studies including radical trapping, isotopic labeling, and density functional theory (DFT) calculations.

Main Results:

  • Achieved regioselective synthesis of deconjugated alkenes from six-membered and larger cyclic acetals.
  • Demonstrated broad substrate scope for both cyclic acetals and alkynes.
  • Obtained moderate to excellent yields and high regioselectivity in product formation.

Conclusions:

  • Established a novel platform for site-selective functionalization of vicinal diols.
  • Highlighted the potential of regioselective hydrogen atom transfer (RHAT)-enabled strategies for C-O bond activation.
  • The proposed mechanism involves a sequential RHAT/radical addition/RHAT/C-O cleavage pathway.