Oxidation of Carbonyl Compounds

Johnston, Eric V.; Bäckvall, Jan‐Erling

doi:10.1002/9783527632039.ch10

Cited by 3 publications

(1 citation statement)

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“…The oxidation of aldehydes to carboxylic acids has been of long-standing interest in synthetic organic chemistry, 14 and is an industrially important process. 15 Compared to different oxidizing reagents used in conventional methods such as Cr( iv )-based Jones oxidation, 16 , 17 Ag( i )-based Tollen's reaction, 18 and Cu( ii )-based Fehling's reaction, 19 molecular oxygen is considered as an ideal oxidant because it is inexpensive, environmentally friendly, 20 and exhibits highly atom-efficient oxidation per weight (100% atom efficiency). 21 Methods to achieve direct and efficient oxidation of aldehydes to carboxylic acids using molecular oxygen as the oxidant under mild conditions are relatively scarce and highly needed, 22 although recently, progress has been made in the development of less expensive transition-metal catalysts for oxidation of aldehydes to carboxylic acids in the bulk.…”

Section: Introductionmentioning

confidence: 99%

Preparative microdroplet synthesis of carboxylic acids from aerobic oxidation of aldehydes

2018

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Section: Introductionmentioning

confidence: 99%

Preparative microdroplet synthesis of carboxylic acids from aerobic oxidation of aldehydes

2018

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Selective One‐Step Aerobic Oxidation of Cyclohexane to ϵ‐Caprolactone Mediated by N‐Hydroxyphthalimide (NHPI)

Wang

Zhang

et al. 2019

ChemCatChem

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dichloroethane (20 mL) were placed into a three-necked round bottom flask (50 mL) equipped with an oxygen balloon and a magnetic stir bar. The mixture was stirred at 40°C for 24 hours. The reaction was monitored by GC instrument. The conversion was calculated on the basis of the peak area ratio of cyclohexane against the internal standard, biphenyl. The product yields were calculated on the basis of the peak area ratio of cyclohexanol, cyclohexanone, and ɛ-caprolactone against the internal standard. Control experiment was conducted in the absence of NHPI.General EPR experiments in different solvents. To a 25 mL Schlenk tube with a magnetic stirrer was added 0.2122 g (2 mmol) of benzaldehyde, 0.0163 g (0.1 mmol) of NHPI and 10 mL of 1,2dichloroethane (DCE). The mixture was stirred at 40°C for 30 min at atmospheric pressure. Thereafter, EPR was measured immediately. The EPR spectra of the reaction solution were obtained by using a computer controlled X-band (9.5 GHz) EPR spectrometer (Bruker A300). The solvent DCE was replaced by CH 3 CN and Toluene. Control experiments were conducted in the absence of benzaldehyde in different solvents. General EPR experiments with NHPI.To a 50 mL three-necked glass flask fitted with a water cooled reflux condenser, a magnetic stir bar and an oxygen balloon was added 0.4245 g (4 mmol) of benzaldehyde and 20 mL of 1,2-dichloroethane (DCE). The mixture was stirred at 40°C for 30 min at atmospheric pressure. Then 0.0326 g (0.2 mmol) of NHPI was added into the mixture and the mixture was stirred for another 30 min. The EPR spectra of the reaction solution (Figure 1(c), green) were obtained by using a computer controlled X-band (9.5GHz) EPR spectrometer (Bruker A300). Thereafter, EPR was measured immediately upon addition of 0.168 g (2 mmol) of cyclohexane into the reaction system (blue). The reaction was continued for 2 h before measuring EPR (red).

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ChemInform Abstract: Oxidation of Carbonyl Compounds

Johnston

Baeckvall

2011

ChemInform

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Oxidation of Carbonyl Compounds

Cited by 3 publications

References 142 publications

Preparative microdroplet synthesis of carboxylic acids from aerobic oxidation of aldehydes

Preparative microdroplet synthesis of carboxylic acids from aerobic oxidation of aldehydes

Selective One‐Step Aerobic Oxidation of Cyclohexane to ϵ‐Caprolactone Mediated by N‐Hydroxyphthalimide (NHPI)

ChemInform Abstract: Oxidation of Carbonyl Compounds

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