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Related Concept Videos

Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.1K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.1K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

4.2K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
4.2K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.3K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.3K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.9K
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.
2.9K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.9K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
1.9K
Prochirality02:05

Prochirality

4.1K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
4.1K

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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
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Sonochemical Protocols for Heterocyclic Synthesis: A Representative Review.

Meena Devi1, Rahul Singh1, Jayant Sindhu2

  • 1Department of Chemistry, Kurukshetra University, Kurukshetra, 136119, India.

Topics in Current Chemistry (Cham)
|February 12, 2022
PubMed
Summary

Green chemistry utilizes sonication to develop sustainable synthetic processes for heterocycles. This approach reduces energy consumption and hazardous chemical use, offering environmental benefits over traditional methods.

Keywords:
Catalyst-freeClay-catalyzedHeterocyclesIonic liquidMulti-component reactionsNano-catalyzedSolid-supported catalystsSonicationUltrasound

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Area of Science:

  • Green Chemistry
  • Organic Synthesis
  • Sonochemistry

Background:

  • Industrial chemical processes contribute significantly to environmental pollution and pose risks to human health.
  • The development of sustainable and environmentally benign synthetic methods is a critical goal for the chemical community.
  • Sonochemistry offers unique properties, including high pressure and temperature generation, making it a valuable tool for green chemistry.

Purpose of the Study:

  • To explore the application of sonication in developing green and sustainable synthetic routes for heterocyclic compounds.
  • To provide mechanistic insights into sono-accelerated heterocyclic synthesis.
  • To compare the advantages of sonochemical methods with conventional approaches.

Main Methods:

  • Ultrasonic irradiation was employed to accelerate various chemical transformations.
  • Synthetic methodologies for heterocyclic core construction under sonication were investigated.
  • Mechanistic studies and comparisons with conventional methods were conducted.

Main Results:

  • Sonication significantly enhances heterocyclic synthesis, offering environmental and process-related advantages.
  • Ultrasound application reduces energy consumption, improves product selectivity, and minimizes the use of hazardous chemicals and solvents.
  • Specific sono-accelerated reactions discussed include aza-Michael, aldol reactions, C-C couplings, oxidation, cycloadditions, and multi-component reactions.

Conclusions:

  • Sonochemistry is a powerful tool for advancing green chemistry principles in organic synthesis.
  • Ultrasonic irradiation provides an efficient and sustainable alternative for the synthesis of diverse heterocyclic compounds.
  • Further development of sono-chemical methods holds great promise for environmentally friendly chemical production.