Addition of N-hydroxyphthalimide and atmospheric oxygen to styrenes using tert-butyl hydroperoxide as a radical initiator

Krylov, Igor B.; Budnikov, Alexander S.; Lastovko, Andrey V.; Ibatov, Yaroslav A.; Nikishin, G. I.; Terent’ev, Alexander O.

doi:10.1007/s11172-019-2577-1

Cited by 14 publications

(12 citation statements)

References 28 publications

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“…15 This trend for intensifi cation of oxidation of alkylaromatic hydrocarbons to HP using the so-called "organocatalysis" is widely acknowledged. [16][17][18] At the same time, this method was not studied previously for the oxidation of p-TBC. The application of N-HPI as the catalyst of p-TBC oxidation makes it possible to increase the conversion of hydrocarbon and the selectivity of HP formation by 2-3 times and 95-98%, respectively, compared to the oxidation in the presence of the hydroperoxide initiator.…”

Section: Resultsmentioning

confidence: 99%

Hydroperoxide method for the synthesis of p-tert-butylphenol

et al. 2021

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The results of studies related to the development of a highly selective three-stage method for the synthesis of p-tert-butylphenol along with acetone are presented. The alkylation of isopropylbenzene with tert-butyl alcohol in the presence of concentrated sulfuric acid makes it possible to obtain only the para-isomer of tert-butylcumene. For the liquid-phase aerobic oxidation of p-tert-butylcumene in the presence of the phthalimide catalysts, the hydrocarbon conversion reaches 45% with a selectivity of hydroperoxide formation of 90-95%. The process of acid decomposition of p-tert-butylcumene hydroperoxide to p-tert-butylphenol and acetone was studied. Conditions providing the production of p-tert-butylphenol in a yield of 90% were found.

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Section: Resultsmentioning

confidence: 99%

Hydroperoxide method for the synthesis of p-tert-butylphenol

et al. 2021

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“…Terent′ev et al described Fe(NO 3 ) 3 /NaNO 2 system for the nitration of pyrazolin‐5‐ones 67 to produce 4‐nitropyrazolin‐5‐ones 68 at room temperature (Scheme ) . The protocol was selective for the 4‐position of pyrazolin‐5‐ones even in the presence of N ‐Ph and allyl substitutions which are otherwise considered to be sensitive towards nitration.…”

Section: Nano2 As Nitrating Agentmentioning

confidence: 99%

Applications of Sodium Nitrite in Organic Synthesis

Mukhopadhyay

Batra

2019

Eur J Org Chem

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Sodium nitrite (NaNO2) is a cheap inorganic reagent that has wide applications in synthetic organic chemistry. The Sandmeyer reaction for transforming amines into diazo derivatives and nitration, including the oxidative ones, are well known and globally used in several industrial processes too. Sodium nitrite is also used in the Nef reaction and Abidi transformation besides several other important reactions. The ability of NaNO2 to produce NO·, NO2, and N2O4 under oxidative conditions has considerably assisted in the discovery of its newer applications. Strikingly, this has resulted in remarkable development in reactions involving NaNO2 as either catalyst or reagent, and this review is an attempt to assimilate them. Wherever possible the mechanistic details associated with the reported reaction/transformation is provided.

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“…5 Peroxides are also employed as radical initiators for polymerizations. 2,6 For synthetic chemistry, oxidation reactions are crucial, and inorganic and organic peroxides, either solo or in the presence of catalysts, play central roles. 1−3 Applications include the oxidation of amines to amides, 7,8 alkane activation, 9,10 epoxidation reactions, 11,12 selective transformations of sulfides to sulfoxides, 13,14 and catalyst-free oxidations of phosphines to their oxides.…”

Section: Introductionmentioning

confidence: 99%

“…Peroxides are ubiquitous in daily life. − They are active ingredients for bleaching in the production of goods and for disinfection in the household, in medicine, and wastewater treatment . Peroxides are also employed as radical initiators for polymerizations. , For synthetic chemistry, oxidation reactions are crucial, and inorganic and organic peroxides, either solo or in the presence of catalysts, play central roles. − Applications include the oxidation of amines to amides, , alkane activation, , epoxidation reactions, , selective transformations of sulfides to sulfoxides, , and catalyst-free oxidations of phosphines to their oxides. , Baeyer–Villiger oxidation is crucial for synthesizing esters from ketones. , …”

Section: Introductionmentioning

confidence: 99%

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Di(hydroperoxy)cycloalkane Adducts of Triarylphosphine Oxides: A Comprehensive Study Including Solid-State Structures and Association in Solution

2020

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Four new di(hydroperoxy)cycloalkane adducts (Ahn adducts) of p-Tol 3 PO (1) and o-Tol 3 PO (2), namely, p-Tol 3 PO•(HOO) 2 C(CH 2 ) 5 (3), o-Tol 3 PO•(HOO) 2 C(CH 2 ) 5 (4), p-Tol 3 PO•(HOO) 2 C(CH 2 ) 6 ( 5), and o-Tol 3 PO•(HOO) 2 C(CH 2 ) 6 ( 6), have been synthesized and fully characterized. Their single crystal X-ray structures have been determined and analyzed. The 31 P NMR data are in accordance with hydrogen bonding of the di(hydroperoxy)alkanes to the PO groups of the phosphine oxides. Due to their high solubility in organic solvents, natural abundance 17 O NMR spectra of 1−6 could be recorded, providing the signals for the PO groups and additionally the two different oxygen nuclei in the O−OH groups in the adducts 3−6. The association and mobility of 3−6 were explored by 1 H DOSY (diffusion ordered spectroscopy) NMR, which indicated persistent hydrogen bonding of the adducts in solution. Competition experiments with phosphine oxides allowed ranking of the affinities of the di(hydroperoxy)cycloalkanes for the different phosphine oxide carriers. On the basis of variable temperature 31 P NMR investigations, the Gibbs energies of activation ΔG ‡ for the adduct dissociation processes of 3−6 at different temperatures, as well as the enthalpy ΔH ‡ and entropy ΔS ‡ of activation, have been determined. IR spectroscopy of 3−6 corroborated the hydrogen bonding, and in the Raman spectra, the ν(O−O) stretching bands have been identified, confirming the presence of peroxy groups in the solid materials. The high solubilities in selected organic solvents have been quantified.

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Addition of N-hydroxyphthalimide and atmospheric oxygen to styrenes using tert-butyl hydroperoxide as a radical initiator

Cited by 14 publications

References 28 publications

Hydroperoxide method for the synthesis of p-tert-butylphenol

Hydroperoxide method for the synthesis of p-tert-butylphenol

Applications of Sodium Nitrite in Organic Synthesis

Di(hydroperoxy)cycloalkane Adducts of Triarylphosphine Oxides: A Comprehensive Study Including Solid-State Structures and Association in Solution

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