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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.8K
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.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.2K
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.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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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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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.9K
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.
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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

4.0K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

3.2K
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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Related Experiment Video

Updated: Apr 17, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Calcium-catalyzed formal [2+2+2] cycloaddition.

Vera J Meyer1, Christoph Ascheberg, Meike Niggemann

  • 1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 18, 2015
PubMed
Summary
This summary is machine-generated.

A novel calcium-catalyzed cycloaddition reaction efficiently synthesizes bicyclic compounds from enynes and aldehydes. This method offers high selectivity and creates complex structures with multiple stereocenters in a single step.

Keywords:
allenescalcium catalysiscarbocationscycloadditioncycloisomerizationenynes

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Intermolecular cycloaddition reactions are crucial for constructing complex organic molecules.
  • Developing efficient and selective catalytic systems for cycloadditions remains a significant challenge in synthetic chemistry.

Purpose of the Study:

  • To present a novel intermolecular [2+2+2] cycloaddition reaction of enynes with aldehydes.
  • To achieve a one-step synthesis of bicyclic building blocks with high stereochemical control using a calcium catalyst.

Main Methods:

  • Utilizing a simple and benign calcium catalyst for the cycloaddition reaction.
  • Investigating the reaction mechanism through mechanistic proposals.

Main Results:

  • The reaction demonstrates excellent chemo-, regio-, and diastereoselectivity.
  • Successfully assembled bicyclic building blocks containing up to three stereocenters from simple precursors.
  • Proposed two distinct mechanistic pathways to account for the observed diastereoselectivity.

Conclusions:

  • A new skeletal rearrangement of enynes enables the formation of valuable bicyclic structures.
  • The developed calcium-catalyzed method provides an efficient route to complex stereodefined molecules.
  • Mechanistic insights were gained through analysis of gold-catalyzed reactions and a proposed cascade pathway.