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Related Concept Videos

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.
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[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
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
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

2.4K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.4K
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

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

5.5K
The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
5.5K
Halogenation of Alkenes02:46

Halogenation of Alkenes

15.4K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
15.4K

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Bicyclo[2.1.1]hexanes via Intramolecular Formal (3+2)-Cycloaddition.

Alexander S Harmata1, Elene Tatunashvili2,1, Abigail Chang1

  • 1Department of Chemistry, University of Michigan, 930 N University Ave, Ann Arbor, MI, 48109, United States.

Angewandte Chemie (International Ed. in English)
|October 11, 2024
PubMed
Summary
This summary is machine-generated.

This study introduces a new method for synthesizing bicyclo[2.1.1]hexanes using a cycloaddition reaction. The resulting bicyclic imines can undergo photo-induced ring opening for stereochemical control.

Keywords:
bicyclo[2.1.1]hexanebicyclo[3.2.1]octanecycloadditioniminephotochemistry

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Bicyclo[2.1.1]hexanes are strained ring systems with unique structural properties.
  • Efficient synthetic routes to these scaffolds are valuable for various chemical applications.

Purpose of the Study:

  • To develop a novel intramolecular formal (3+2) cycloaddition for bicyclo[2.1.1]hexane synthesis.
  • To explore the scope and limitations of the developed synthetic methodology.

Main Methods:

  • Intramolecular formal (3+2) cycloaddition reaction.
  • Utilizing allylated cyclopropanes with a 4-nitrobenzimine substituent.
  • Employing both activated and unactivated alkenes as reaction partners.

Main Results:

  • Successful synthesis of bicyclo[2.1.1]hexanes.
  • Demonstrated tolerance of diverse alkene substrates.
  • Observed photo-induced ring opening of the bicyclic imine products.

Conclusions:

  • The developed cycloaddition provides a new pathway to bicyclo[2.1.1]hexanes.
  • The photo-induced ring opening offers a method for epimerization of stereocenters.
  • This methodology expands the synthetic toolkit for accessing complex bicyclic structures.