Interrupted Nef and Meyer Reactions: A Growing Point for Diversity-Oriented Synthesis Based on Nitro Compounds
1N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow 119991, Russia.
Molecules (Basel, Switzerland)
|January 21, 2023
Summary
Interrupted Nef and Meyer reactions offer new synthetic pathways for nitro compounds. These less common methods redirect reactions using nucleophiles, expanding synthetic potential in organic chemistry.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- The Nef reaction (nitro to carbonyl group conversion) and Meyer reaction are fundamental transformations for aliphatic nitro compounds.
- Interrupted versions of these reactions, where external nucleophiles redirect the pathway, are less explored but synthetically valuable.
Purpose of the Study:
- To review and summarize examples of interrupted Nef and Meyer reactions.
- To analyze the prospects of these interrupted reactions in diversity-oriented organic synthesis.
Main Methods:
- Literature review of interrupted Nef and Meyer reactions.
- Analysis of synthetic applications and potential in organic synthesis.
Main Results:
- Compilation of known examples of interrupted Nef and Meyer reactions.
- Demonstration of how these reactions increase the synthetic utility of nitro compounds.
Conclusions:
- Interrupted Nef and Meyer reactions significantly enhance the synthetic potential of nitro compounds.
- These methodologies hold promise for diversity-oriented synthesis, offering novel routes to complex molecules.
![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
01:12Preparation of Nitriles
2.1K
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...
2.1K
01:30Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
3.9K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
3.9K
01:20Electrophilic Aromatic Substitution: Nitration of Benzene
6.3K
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.
6.3K
01:19Nitrosation of Enols
3.2K
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.
3.2K
01:26Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
3.5K
α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
3.5K
01:29Preparation of Amines: Reduction of Oximes and Nitro Compounds
3.9K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
3.9K