Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

9.8K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
9.8K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

5.5K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
5.5K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.5K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.5K
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

2.8K
The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
2.8K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.1K
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).
2.1K
Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

2.4K
The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
2.4K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Phosphine vs DBU-Catalyzed Annulation Reactions of β'-Acetoxy Allenoates with Acyl-Tethered Benzothiazole Bisnucleophiles: (4 + 3) or (4 + 1) vs (3 + 3) Annulation.

The Journal of organic chemistry·2024
Same author

[Au]-Catalyzed Cyclization of Propargyl-Tethered Ene-Amides: Substrate-Dependent Access to Tetrasubstituted Pyrroles, Aminophenols, and Dihydropyridines.

The Journal of organic chemistry·2024
Same author

δ-Acetoxy Allenoate as a <i>5C</i>-Synthon in Domino-Annulation with Sulfamidate Imines: Ready Access to Coumarins.

The Journal of organic chemistry·2023
Same author

(3 + 3) Annulation of acetoxy allenoates with enolisable carbonyl substrates leading to fused pyrans.

Organic & biomolecular chemistry·2023
Same author

DBU-Catalyzed Ring Expansion or Ene-amine Formation Involving δ-Acetoxy Allenoates and <i>N</i>-Sulfonyl Hydrazides.

Organic letters·2023
Same author

Cu(II)-Catalyzed Decarboxylative (4 + 2) Annulation of Coumarin-3-Carboxylic Acids with In Situ Generated α,β-Unsaturated Carbonyl Compounds from <i>tert</i>-Propargylic Alcohols.

Organic letters·2023

Related Experiment Video

Updated: May 16, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

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

Published on: June 21, 2017

7.3K

Acetoxy allenoates as emerging synthons in annulation/cycloaddition reactions.

K C Kumara Swamy1, Sachin Chauhan1, A Sanjeeva Kumar1

  • 1School of Chemistry, University of Hyderabad, Hyderabad 500 046, Telangana, India. kckssc@uohyd.ac.in.

Chemical Communications (Cambridge, England)
|April 4, 2025
PubMed
Summary

Acetoxy allenoates generate electrophilic diene-phosphonium/ammonium intermediates, enabling diverse cycloaddition reactions. This review explores their unique reactivity and synthesis of complex cyclic compounds.

More Related Videos

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

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

8.0K
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.2K

Related Experiment Videos

Last Updated: May 16, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

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

Published on: June 21, 2017

7.3K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

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

8.0K
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.2K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Normal allenoates react with nucleophiles to form dipolar intermediates.
  • Acetoxy allenoates possess a leaving group, altering their reaction pathways.

Purpose of the Study:

  • To review the unique chemistry of acetoxy allenoates.
  • To highlight their role in generating electrophilic intermediates.

Main Methods:

  • Review of literature on acetoxy allenoate chemistry.
  • Analysis of reaction mechanisms involving diene-phosphonium/ammonium intermediates.

Main Results:

  • Acetoxy allenoates form electrophilic diene-phosphonium/ammonium intermediates.
  • These intermediates undergo cycloaddition/annulation with bisnucleophiles.
  • Multifunctional hetero- and homo-cycles are synthesized efficiently.

Conclusions:

  • The electrophilicity of intermediates is key to their reactivity.
  • Acetoxy allenoates represent a significant emerging class of substrates.
  • Their chemistry offers a versatile route to complex cyclic structures.