One pot synthesis of cyclohexanone oxime from nitrobenzene using a bifunctional catalyst
Paula Rubio-Marqués1, Juan Carlos Hernández-Garrido, Antonio Leyva-Pérez
1Instituto de Tecnología Química, Universidad Politécnica de Valencia-Consejo Superior de Investigaciones Científicas (UPV-CSIC.), Avda. De los Naranjos S/N, Valencia, Spain. anleyva@itq.upv.es acorma@itq.upv.es.
Chemical Communications (Cambridge, England)
|November 26, 2013
Summary
This study presents a one-pot synthesis of cyclohexanone oxime from nitrobenzene using palladium and gold nanoparticles. The efficient catalytic process achieves a 97% yield under mild conditions.
Area of Science:
- Catalysis
- Organic Synthesis
- Nanomaterials
Background:
- Nitrobenzene reduction is a key transformation in organic synthesis.
- Developing efficient and selective catalytic systems is crucial for sustainable chemistry.
Purpose of the Study:
- To develop a highly efficient one-pot method for cyclohexanone oxime synthesis.
- To investigate the catalytic mechanism using palladium and gold nanoparticles.
Main Methods:
- One-pot reaction of nitrobenzene with hydrogen gas.
- Catalysis using palladium and gold nanoparticles supported on carbon.
- Reaction conducted at 60 °C.
Main Results:
- Achieved a 97% yield of cyclohexanone oxime.
- Identified reaction intermediates and catalytically active species.
- Elucidated a multi-step catalyzed mechanism.
Conclusions:
- Palladium and gold nanoparticles on carbon provide an effective catalytic system for nitrobenzene to cyclohexanone oxime conversion.
- The one-pot reaction offers a high-yield and potentially scalable route.
- Understanding the mechanism aids in further catalyst development.
![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
01:19Nitrosation of Enols
9.9K
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.
9.9K
01:29Preparation of Amines: Reduction of Oximes and Nitro Compounds
3.7K
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,...
3.7K
01:27Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
2.3K
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).
2.3K
03:00Preparation of Epoxides
7.7K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy...
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy...
7.7K
01:20Electrophilic Aromatic Substitution: Nitration of Benzene
7.5K
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.
7.5K
02:26Base-Catalyzed Ring-Opening of Epoxides
8.7K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
8.7K