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Nitrosation of Enols

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

Electrophilic Aromatic Substitution: Nitration of Benzene

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

Preparation of Nitriles

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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

meta-Directing Deactivators: –NO2, –CN, –CHO, –&NoBreak;CO2R, –COR, –CO2H

meta-Directing Deactivators: –NO₂, –CN, –CHO, –⁠CO₂R, –COR, –CO₂H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...

Nitriles to Ketones: Grignard Reaction

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Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard reagent...

Preparation of Carboxylic Acids: Hydrolysis of Nitriles

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Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.

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Functionalization of corroles: the nitration reaction.

Manuela Stefanelli¹, Marco Mastroianni, Sara Nardis

¹Dipartimento di Scienze e Tecnologie Chimiche, Università di Roma Tor Vergata, via della Ricerca Scientifica 1, 00133 Rome, Italy.

Inorganic Chemistry

|November 8, 2007

Summary

Silver(III) corrole complexes undergo regioselective nitration with silver nitrite, forming novel nitro-substituted silver(III) corrole complexes. This reaction mechanism involves a pi-cation radical intermediate attacked by nitrite ions.

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Area of Science:

Coordination Chemistry
Organic Synthesis
Spectroscopy

Background:

Corroles are macrocyclic ligands with diverse coordination chemistry.
Peripheral functionalization of corrole complexes is crucial for tuning their properties.

Purpose of the Study:

To investigate the nitration reaction of meso-triarylcorroles with silver nitrite.
To elucidate the reaction mechanism and characterize the resulting nitro-substituted silver(III) corrole complexes.
To explore the electrochemical properties of these novel complexes.

Main Methods:

Reaction of meso-triarylcorroles with silver nitrite (AgNO2).
Characterization of products using X-ray crystallography, cyclic voltammetry, and spectroelectrochemistry.
Comparative studies with copper corrole complexes and sodium nitrite (NaNO2).

Main Results:

Concomitant metalation and peripheral substitution yielding nitro-substituted silver(III) corrole complexes.
High regioselectivity observed, exclusively forming the 3-nitro derivative.
Identification of a pi-cation radical intermediate, confirmed by copper corrole reactions.
Successful synthesis and characterization of a novel meso-substituted silver corrole derivative, (NO2)3AMCorAg.
Elucidation of electron transfer sites through electrochemical studies.

Conclusions:

The reaction of meso-triarylcorroles with AgNO2 provides a regioselective route to nitro-substituted silver(III) corrole complexes.
The reaction proceeds via a pi-cation radical intermediate, showcasing the reactivity of corrole complexes.
The study reports the first meso-substituted silver corrole derivative, expanding the scope of corrole chemistry.