Sulfonic peracids — III. Heteroatom oxidation and chemoselectivity

Kluge, Ralph; Schulz, Manfred; Liebsch, Stephan

doi:10.1016/0040-4020(96)00202-5

Cited by 30 publications

(13 citation statements)

References 14 publications

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“…Further we applied optimized reaction for oxidation of alicyclic and alkyl amine derivatives. The oxidation smoothly proceeded to give corresponding oxime in good yield (Table 3, entries [16][17][18][19][20]. Typically maximum yield was obtained for cyclohexyl and cyclopentyl amine (Table 3, entries 16, 17) as compared to acyclic aliphatic amines.…”

Section: Resultsmentioning

confidence: 98%

Highly efficient and stable peracid for rapid and selective oxidation of aliphatic amines to oximes

2015

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A novel, transition-metal free, rapid approach for selective oxidation of aliphatic and benzylic amine to oxime is described. The dodecanebis(peroxoic acid)-DMF combination efficiently oxidize various aliphatic amines at 50 °C temperature to give 100% conversion in 20 min with high oxime selectivity. The peroxy acid used here show exceptional stability at room temperature and non-shock sensitive in nature, which was confirmed by differential scanning colorimetric (DSC) analysis.

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Section: Resultsmentioning

confidence: 98%

Highly efficient and stable peracid for rapid and selective oxidation of aliphatic amines to oximes

2015

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“…The comparatively low molar ratio of TSA to PANI ( y = 0.25) is difficult to explain. However, it is known25–27 that TSA can be used to support oxidation reactions, changing the mechanism of the oxidation and influencing the chemical structure of the final products. For example, the oxidation of aniline with hydrogen peroxide in the presence of TSA yields almost exclusively azoxybenzene 27.…”

Section: Resultsmentioning

confidence: 99%

“…However, it is known25–27 that TSA can be used to support oxidation reactions, changing the mechanism of the oxidation and influencing the chemical structure of the final products. For example, the oxidation of aniline with hydrogen peroxide in the presence of TSA yields almost exclusively azoxybenzene 27. This suggests that PANI molecules produced by oxidation polymerization in the presence of TSA can possess more structural defects than standard PANI.…”

Section: Resultsmentioning

confidence: 99%

Precipitation polymerization of aniline in the presence of water‐soluble organic acids

Laska

Widlarz

Woźny

2002

J. Polym. Sci. A Polym. Chem.

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The precipitation polymerization of aniline in the presence of organic acids, including toluene‐4‐sulfonic acid, phenylphosphonic acid, 4‐aminophenylphosphonic acid, and acetophosphonic acid, led in one step to conductive polyaniline. The polyaniline showed very good affinity for water and was easily modified to be water‐soluble. In comparison with the widely studied postpolymerization of doped polyaniline, this reaction allowed reasonably good conductivity to be achieved at a lower acid/polyaniline ratio. Moreover, the easy in situ incorporation of the dopant into the polymer structure caused high stability of the created salt; that is, no dedoping was observed after it was washed with water, methanol, or other solvents. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 3562–3569, 2002

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“…Therefore, many methods have been reported for the synthesis of azoxybenzene. Traditional methods heavily rely on stoichiometric reduction and oxidation such as reduction of nitro and nitroso aromatic compounds by using sodium bis(trimethylsilyl)amide [2] and potassium borohydride, [3] and oxidation of anilines with stoichiometric oxidants of sulfonic peracids, [4] Bu 4 N-HSO 5 , [5] and m-chloroperoxybenzoic acid. [6] However, the use of stoichiometric reagents makes these processes environmentally unfriendly.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Azoxybenzenes by Selective Oxidation of Anilines on Titanium Silicate Molecular Sieves

Song¹,

Feng²,

Han³

et al. 2019

Chin. J. Org. Chem.

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A convenient method for improving the conversion and selectivity of aniline to azoxybenzene by adjusting the ratio of silicon to titanium of TS-1 is reported. Over TS-1 (80), aryl anilines are transformed into the corresponding azoxybenzenes in good yields with H 2 O 2 as the oxidant. The effect of different reaction parameters like molar ratio of H 2 O 2 to aniline, solvent and the activity in catalyst recycling has been studied.

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Sulfonic peracids — III. Heteroatom oxidation and chemoselectivity

Cited by 30 publications

References 14 publications

Highly efficient and stable peracid for rapid and selective oxidation of aliphatic amines to oximes

Highly efficient and stable peracid for rapid and selective oxidation of aliphatic amines to oximes

Precipitation polymerization of aniline in the presence of water‐soluble organic acids

Synthesis of Azoxybenzenes by Selective Oxidation of Anilines on Titanium Silicate Molecular Sieves

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