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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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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

アンフォテリック α-ボリルアルデヒド

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
まとめ
この要約は機械生成です。

研究者は,α-ボリルアルデヒドと呼ばれる新しい種類の安定分子を開発しました. これらの化合物は,非自然なアミノ酸を含む複雑な有機分子を合成するための多用途な構成要素です.

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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

関連する実験動画

Last 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

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • 合成化学 合成化学とは
  • 分子合成による分子合成です.

背景:

  • 機能化されたボロン酸誘導体を合成するための確立されたプロトコルは限られている.
  • 多様な有機分子にアクセスするための新しい合成経路が必要である.

研究 の 目的:

  • 安定した分子,α-ボリルアルデヒドの新しいクラスについて報告します.
  • α-ボリルアルデヒドの汎用性の高い合成構成要素としての有用性を実証する.

主な方法:

  • 1,2-ボリル遷移とエポキシド分裂によるオキラニルN-メチリミノアセチルボロナートからα-ボリルアルデヒドの製造.
  • α-ボリルアルデヒドを用いて,化学選択的変換を行う.

主要な成果:

  • 新種の安定分子であるα-ボリルアルデヒドの合成に成功した.
  • ボリルイミン,アルケーン,アルコール,酸,エノルエーテル,エナミドを含む幅広い機能化されたボロン酸誘導体へのアクセスを実証した.
  • シリロキシおよびアミドビニルボロナートから機能化された非自然なアミノ酸の簡単な合成が達成されました.

結論:

  • α-ボリルアルデヒドは,合成有機化学の重要な進歩を表しています.
  • これらの新しい構成要素は,以前に合成が困難または不可能であった複雑な分子への効率的な経路を提供します.
  • 化学合成におけるα-ボリルアルデヒドの潜在力は,特に非自然的なアミノ酸へのアクセスのために,かなりのものです.