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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
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...
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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.
Conjugate Addition of Enolates: Michael Addition01:08

Conjugate Addition of Enolates: Michael Addition

The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition reactions of active methylene compounds, such as β-diketones, β-keto esters, β-keto nitriles, and α-nitro ketones, are called Michael addition reactions.

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Related Experiment Video

Updated: Jul 4, 2026

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

Amine-Enabled Electron Donor-Acceptor Complex Catalysis for Cyclopropanation.

Rahul Tarkase1, Basavarajagouda E Patil1, Komal Pal1

  • 1Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, 400076, India.

Organic Letters
|July 3, 2026
PubMed
Summary
This summary is machine-generated.

This study introduces a new catalyst-free method for cyclopropanation using electron donor-acceptor (EDA) complexes and visible light. The novel amine-enabled process efficiently transforms alkenes under mild conditions.

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

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Last Updated: Jul 4, 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

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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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

Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Radical Reactions

Background:

  • Electron donor-acceptor (EDA) complexes offer a catalyst-free approach for visible-light-driven radical reactions.
  • Developing efficient methods for alkene functionalization remains a key challenge in organic synthesis.

Purpose of the Study:

  • To report a novel amine-enabled, EDA-mediated cyclopropanation of alkenes.
  • To demonstrate a catalyst-free visible-light-driven radical transformation using a ground-state charge-transfer complex.

Main Methods:

  • Utilized diiodomethane and amine to form a ground-state charge-transfer complex.
  • Employed visible-light irradiation for the cyclopropanation reaction.
  • Conducted comprehensive mechanistic studies including EPR, cyclic voltammetry, UV-Vis, quantum yield, and DFT.

Main Results:

  • Achieved efficient cyclopropanation of alkenes under mild conditions.
  • Demonstrated broad functional-group tolerance for the developed method.
  • Mechanistic studies confirmed an EDA-mediated radical pathway.

Conclusions:

  • The reported method provides a versatile and efficient route for alkene cyclopropanation.
  • The findings highlight the potential of EDA complexes in visible-light-driven organic transformations.
  • This work expands the scope of catalyst-free radical reactions.