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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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 halogen to form a...
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

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 at the stage of...
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...
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the bromine molecule...
Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

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...
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...

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Updated: May 30, 2026

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
06:26

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

Published on: August 17, 2018

Amphoteric α-boryl aldehydes.

Zhi He1, Andrei K Yudin

  • 1Davenport Research Laboratories, Department of Chemistry, University of Toronto, Ontario, Canada.

Journal of the American Chemical Society
|August 4, 2011
PubMed
Summary
This summary is machine-generated.

Researchers developed a new class of stable molecules called α-boryl aldehydes. These compounds are versatile building blocks for synthesizing complex organic molecules, including unnatural amino acids.

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Published on: November 30, 2022

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Molecule Synthesis

Background:

  • Established protocols for synthesizing functionalized boronic acid derivatives are limited.
  • There is a need for novel synthetic routes to access diverse organic molecules.

Purpose of the Study:

  • To report a new class of stable molecules, α-boryl aldehydes.
  • To demonstrate the utility of α-boryl aldehydes as versatile synthetic building blocks.

Main Methods:

  • Preparation of α-boryl aldehydes from oxiranyl N-methyliminodiacetyl boronates via 1,2-boryl migration and epoxide scission.
  • Utilizing α-boryl aldehydes for chemoselective transformations.

Main Results:

  • Successfully synthesized α-boryl aldehydes, a new class of stable molecules.
  • Demonstrated access to a wide range of functionalized boronic acid derivatives, including boryl imines, alkenes, alcohols, acids, enol ethers, and enamides.
  • Facile synthesis of functionalized unnatural amino acids from silyloxy and amido vinyl boronates was achieved.

Conclusions:

  • α-boryl aldehydes represent a significant advancement in synthetic organic chemistry.
  • These novel building blocks offer efficient routes to complex molecules previously difficult or impossible to synthesize.
  • The potential of α-boryl aldehydes in chemical synthesis is substantial, particularly for accessing unnatural amino acids.