5- and 10-oxocorroles from β-octaalkylcorroles.
Lorena Di Zazzo1, Sara Nardis1, Fabrizio Caroleo1
1Department of Chemical Science and Technologies, University of Rome Tor Vergata, via della Ricerca Scientifica 1, Rome 00133, Italy. nardis@scienze.uniroma2.it.
Chemical Communications (Cambridge, England)
|November 29, 2023
Summary
Zinc ions react with β-octaalkylcorroles, forming oxidized oxocorroles. Spectroscopic analysis reveals their antiaromatic nature, paving the way for further oxocorrole chemistry research.
Area of Science:
- Inorganic Chemistry
- Organic Chemistry
- Materials Science
Background:
- Corroles are macrocyclic ligands with unique electronic properties.
- Oxidation of macrocycles can lead to novel chemical structures and functionalities.
- Understanding the reactivity of β-octaalkylcorroles is crucial for developing new materials.
Purpose of the Study:
- To investigate the reaction of Zn ions with β-octaalkylcorroles.
- To characterize the resulting oxidized macrocyclic products.
- To explore the electronic properties and potential applications of oxocorroles.
Main Methods:
- Reaction of Zn ions with β-octaalkylcorroles under aerobic conditions.
- Isolation and purification of the resulting oxocorrole products.
- Spectroscopic characterization (e.g., NMR, UV-Vis, Mass Spectrometry) to confirm structure and properties.
Main Results:
- Formation of a mixture of 5- and 10-oxocorroles from the reaction.
- Spectroscopic data confirmed the presence of antiaromatic character in the synthesized oxocorroles.
- A straightforward synthetic route to oxocorroles was established.
Conclusions:
- The reaction of Zn ions with β-octaalkylcorroles provides a viable route to oxocorroles.
- The synthesized oxocorroles exhibit antiaromaticity, offering a new class of compounds for study.
- This work establishes a foundation for future investigations into oxocorrole chemistry and applications.
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Related Concept Videos
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
10.3K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.3K
02:36Oxymercuration-Reduction of Alkenes
7.6K
Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
7.6K
01:27Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
2.2K
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).
2.2K
01:33Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
3.8K
Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
3.8K
01:46Oxidative Cleavage of Alkenes: Ozonolysis
10.5K
In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
10.5K
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
18.1K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
18.1K