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Related Concept Videos

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...
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Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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...
Multiple Halogenation of Methyl Ketones: Haloform Reaction01:28

Multiple Halogenation of Methyl Ketones: Haloform Reaction

A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic acyl substitution.
Acid Halides to Alcohols: Grignard Reaction01:15

Acid Halides to Alcohols: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...

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Updated: May 26, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Halogenated Reagents in the Ugi Reaction: From Rearrangement Reactions to Ketal Synthesis.

Beatriz González-Saiz1, Carlos Cámara-Herrero1, Sandra Díaz-Cabrera2

  • 1Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Burgos 09001, Spain.

ACS Omega
|May 25, 2026
PubMed
Summary

Researchers developed a new Ugi/postcondensation method to create conformationally restricted morpholines. This strategy efficiently synthesizes complex heterocyclic compounds, including precursors for 4-hydroxypyroglutamic acid derivatives.

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Published on: November 27, 2015

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Last Updated: May 26, 2026

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12:27

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Published on: November 27, 2015

Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Heterocyclic Chemistry

Background:

  • The morpholine scaffold is crucial in medicinal chemistry.
  • Synthesizing conformationally restricted morpholine systems presents significant challenges.

Purpose of the Study:

  • To develop a novel and efficient synthetic strategy for accessing conformationally restricted morpholines.
  • To demonstrate the diastereoselective synthesis of fused and bridged morpholines.

Main Methods:

  • Employed a Ugi/postcondensation reaction sequence.
  • Combined aliphatic halogenated reagents with arylglyoxals.
  • Achieved diastereoselective synthesis of morpholine derivatives.

Main Results:

  • Successfully synthesized fused and bridged morpholines with ketal functionalities.
  • Demonstrated the utility of these derivatives as precursors to 4-hydroxypyroglutamic acid.
  • Highlighted the synthetic versatility and efficiency of the developed approach.

Conclusions:

  • The Ugi/postcondensation strategy provides a facile route to complex heterocyclic structures.
  • This method offers rapid access to valuable morpholine derivatives for medicinal chemistry applications.