Phthalimide‐<i>N</i>‐oxyl (PINO) Radical, a Powerful Catalytic Agent: Its Generation and Versatility Towards Various Organic Substrates

Coseri, Sergiu

doi:10.1080/01614940902743841

Cited by 209 publications

(144 citation statements)

References 160 publications

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“…Reac Kinet Mech Cat (2013) 110: 15-30 25 A similar influence of electron-donating substituents on the NHPI-catalyzed oxidation has been reported for toluene and ethylbenzene derivatives [24][25][26]. However, to the best of our knowledge, no such data are available for isopropylarenes.…”

Section: Oxidation Processes Of Hydrocarbons 1-7mentioning

confidence: 65%

Aerobic oxidation of isopropylaromatic hydrocarbons to hydroperoxides catalyzed by N-hydroxyphthalimide

Orlińska

Zawadiak

2013

Reac Kinet Mech Cat

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The oxidations of cumene, 4-isopropylbiphenyl, 1-methoxy-4-(1-methylethyl)benzene, 2-isopropylnaphthalene, 2-methoxy-6-(1-methylethyl)naphthalene, 2,6-diisopropylnaphthalene and 4,4 0 -diisopropylbiphenyl to the corresponding hydroperoxides with oxygen, at 60°C, in the presence of N-hydroxyphthalimide (NHPI) and AIBN have been performed. Process inhibition was observed at temperatures above 60°C resulting in lower conversion. A favorable effect of electron-donating substituents (methoxy, phenyl) on the reaction rate were described. NHPI was separated from the cumene oxidation product and recycled 5 times. It has been demonstrated that oxygen can be replaced by air.

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Section: Oxidation Processes Of Hydrocarbons 1-7mentioning

confidence: 65%

Aerobic oxidation of isopropylaromatic hydrocarbons to hydroperoxides catalyzed by N-hydroxyphthalimide

Orlińska

Zawadiak

2013

Reac Kinet Mech Cat

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“…[9][10][11][12] NHPI-catalyzed oxidation of hydrocarbons, (including cumene oxidation with oxygen), have been performed under mild conditions, and high yields as well as high selectivities of products have been achieved. In oxidation processes, PINO radical which is formed in-situ from NHPI, abstracts hydrogen atom from oxidized hydrocarbon much faster, than alkylperoxy radicals in non-catalytic processes (Figure 2).…”

Section: Rooh + R'h → R'oor + Roh + H 2 O (1)mentioning

confidence: 99%

<i>N</i>-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide

Konopińska¹

2017

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Cumene oxidation with 1-methyl-1-phenylethyl hydroperoxide catalyzed by N-hydroxyphthalimide or its derivatives and transition metal salts has been studied. Effects of the type of metal compound (Co(II), Mn(II) or Cu(II) chloride, acetate or acetylacetonate), amounts of N-hydroxyphthalimide and metal salt as well as temperature were established. The highest yields of dicumyl peroxide (48-54%) were obtained, when reaction was performed at 60-70°C, in the presence of the NHPI/CuCl 2 catalytic system, in acetonitrile as a solvent. Similar yield of dicumyl peroxide (43%) was obtained in solvent-free medium.

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“…This compound is a weak acid (pK a = 6.1) [3,4] and has a variety of practical uses. Recently, it has been used as a catalyst in oxidation processes, via the phthalimide N-oxyl radical [5] (known as PINO).…”

Section: Introductionmentioning

confidence: 99%

New N-aryloxy-phthalimide derivatives. Synthesis, physico-chemical properties, and QSPR studies

Tudose¹,

Badea

Cãproiu³

et al. 2010

Open Chemistry

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Abstract:Starting from N-hydroxyphthalimide 1 and the reactive fluoro-or chloro-nitroaryl derivatives 2, 3 and 4a-e (2-chloro-3,5-dinitropyridine; 3, NBD-chloride; 4a, 1-fluoro-2,4-dinitrobenzene; 4b, picryl chloride; 4c, 4-chloro-3,5-dinitrobenzotrifluoride; 4d, 2-chloro-3,5-dinitrobenzotrifluoride; 4e, 4-chloro-3,5-dinitrobenzoic acid) the corresponding N-(2-nitroaryloxy)-phthalimide derivatives 5a-e, or 6 and 7 were obtained and characterized by IR, UV-Vis 1 H-NMR and 13 C-NMR spectroscopy. The TLC behavior and the hydrophobicity of these derivatives have been experimentally evaluated by R M0 parameters (using RP-TLC). The experimental R M0 parameters were compared with the calculated partition coefficient, log P. A QSPR study was also performed to establish possible correlations between the structure and physical properties (λ max and R M0 ) of compounds 5a-e, 6, and 7.

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Phthalimide‐N‐oxyl (PINO) Radical, a Powerful Catalytic Agent: Its Generation and Versatility Towards Various Organic Substrates

Cited by 209 publications

References 160 publications

Aerobic oxidation of isopropylaromatic hydrocarbons to hydroperoxides catalyzed by N-hydroxyphthalimide

Aerobic oxidation of isopropylaromatic hydrocarbons to hydroperoxides catalyzed by N-hydroxyphthalimide

<i>N</i>-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide

New N-aryloxy-phthalimide derivatives. Synthesis, physico-chemical properties, and QSPR studies

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Phthalimide‐N‐oxyl (PINO) Radical, a Powerful Catalytic Agent: Its Generation and Versatility Towards Various Organic Substrates

Cited by 209 publications

References 160 publications

Aerobic oxidation of isopropylaromatic hydrocarbons to hydroperoxides catalyzed by N-hydroxyphthalimide

Aerobic oxidation of isopropylaromatic hydrocarbons to hydroperoxides catalyzed by N-hydroxyphthalimide

&lt;i&gt;N&lt;/i&gt;-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide

New N-aryloxy-phthalimide derivatives. Synthesis, physico-chemical properties, and QSPR studies

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<i>N</i>-Hydroxyphthalimide as a Catalyst of Cumene Oxidation with Hydroperoxide