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Related Concept Videos

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Reactivity of Enols01:18

Reactivity of Enols

Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is governed by factors like...
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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).

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Updated: May 19, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Direct allenol-based stereocontrolled access to substituted (E)-1,3-enynes.

Benito Alcaide1, Pedro Almendros, Teresa Martínez del Campo

  • 1Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain. alcaideb@quim.ucm.es

Organic & Biomolecular Chemistry
|August 21, 2012
PubMed
Summary

A new stereoselective synthesis method creates valuable (E)-2-aryl-but-1-en-3-ynes from aryl-substituted α-allenols. This efficient reaction yields tetrasubstituted alkenes using a simple AcCl-NaOH system.

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Stereoselective synthesis is crucial for creating complex organic molecules.
  • Alkenes and alkynes are fundamental building blocks in organic synthesis.

Purpose of the Study:

  • To develop a novel stereoselective synthesis of 1-substituted (E)-2-aryl-but-1-en-3-ynes.
  • To explore the utility of aryl-substituted α-allenols in this transformation.

Main Methods:

  • Treatment of aryl-substituted α-allenols with acetyl chloride (AcCl) and sodium hydroxide (NaOH) in an aqueous system.
  • Analysis of the reaction products to confirm stereoselectivity and structure.

Main Results:

  • Successful stereoselective synthesis of 1-substituted (E)-2-aryl-but-1-en-3-ynes.
  • Formation of tetrasubstituted alkenes was achieved.
  • The reaction proceeds via elimination of acetic acid from an intermediate α-allenic acetate.

Conclusions:

  • A facile and stereoselective synthetic route to (E)-2-aryl-but-1-en-3-ynes has been established.
  • The AcCl-NaOH system provides an efficient method for synthesizing these valuable compounds.
  • The proposed mechanism involving acetic acid elimination offers insight into the reaction pathway.