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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.5K
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.
3.5K
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
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.0K
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.
2.0K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.1K
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.
10.1K
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
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

8.2K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
8.2K

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Updated: Jun 13, 2025

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Simultaneous Cycloadditions in the Solid State via Supramolecular Assembly.

Navkiran Juneja1, Gary C George2, Kristin M Hutchins2,3

  • 1Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, 79409, United States.

Angewandte Chemie (International Ed. in English)
|September 10, 2024
PubMed
Summary
This summary is machine-generated.

Researchers achieved simultaneous orthogonal cycloaddition reactions in a single crystal. This supramolecular design offers high control over chemical transformations, unlike solution-state reactions.

Keywords:
Crystal engineeringCycloreversionSelf-assemblySolid-state cycloadditionsSupramolecular chemistry

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Area of Science:

  • Solid-state chemistry
  • Supramolecular chemistry
  • Organic synthesis

Background:

  • Crystalline-state reactions offer high control over product stereochemistry and regiochemistry due to molecular self-assembly.
  • However, solid-state reactions are less common than solution reactions due to limited molecular motion and reactivity.
  • Typically, only one reaction type occurs in crystalline-phase transformations, often requiring a sacrificial template molecule.

Purpose of the Study:

  • To demonstrate the first system capable of undergoing two distinct and orthogonal cycloaddition reactions simultaneously within a single crystalline solid.
  • To achieve controlled orthogonal reactivity through supramolecular self-assembly without a sacrificial template.
  • To explore the application of dually-reactive crystalline systems for supramolecular solar thermal energy storage.

Main Methods:

  • Design of two molecules with different reactive moieties that self-assemble in the crystalline state.
  • Utilizing UV light to initiate simultaneous [2+2] and [4+4] cycloaddition reactions.
  • Comparing crystalline-state reaction outcomes with simultaneous solution-state reactions.

Main Results:

  • Achieved simultaneous, regiospecific, and stereospecific [2+2] and [4+4] cycloadditions in high yield within a single crystal.
  • Demonstrated orthogonal reactivity through well-controlled supramolecular self-assembly without a sacrificial template.
  • Solution-state reactions yielded a mixture of isomers in low yield, highlighting the advantage of crystalline-state control.

Conclusions:

  • Established a fundamental chemical approach for achieving orthogonal reactivity in the crystalline state.
  • Highlighted the potential for complex and reversible chemical transformations through supramolecular design in solids.
  • Showcased the utility of dually-reactive crystalline systems for advanced applications like solar thermal energy storage.