Nitro and related groups

Adams, Joseph P.

doi:10.1039/b009711j

Cited by 64 publications

(17 citation statements)

References 122 publications

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“…The equilibrium between 3 a and the 4a‐amino adduct results in a higher catalyst loading being required. This catalytic oxidative transformation of secondary amines into nitrones is compatible with the other catalytic transformations using a catalyst such as Na 2 WO 4 44, 45 and SeO 2 46 for the synthesis of nitrones, which are highly valuable synthetic intermediates for various nitrogen‐containing compounds owing to their high reactivity toward 1,3‐dipolar cycloadditions and nucleophilic addition reactions 47–49. Notably, the oxidation of N ‐hydroxylamine 27 , which bears an optically active sulfoxide, occurred efficiently to give the corresponding nitrone 28 without loss of optical purity (Table 3, entry 5).…”

Section: Resultsmentioning

confidence: 72%

Flavin‐Catalyzed Oxidation of Amines and Sulfides with Molecular Oxygen: Biomimetic Green Oxidation

Imada

Iida

Ono

et al. 2006

Chemistry An Asian Journal

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Flavin-catalyzed green oxidation of heteroatom compounds such as sulfides and amines with molecular oxygen and even air in the presence of hydrazine monohydrate in a fluorous solvent such as 2,2,2-trifluoroethanol at room temperature gives the corresponding oxidation products highly efficiently and selectively along with water and molecular nitrogen, which are environmentally benign by-products. The proposed reaction mechanism is based on the kinetics, solvent effect, and redox properties of flavin catalysts.

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Section: Resultsmentioning

confidence: 72%

Flavin‐Catalyzed Oxidation of Amines and Sulfides with Molecular Oxygen: Biomimetic Green Oxidation

Imada

Iida

Ono

et al. 2006

Chemistry An Asian Journal

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“…Nitro and hydroxy compounds can be formed by oxidation and/or further hydrolysis of amines,19–26 especially in heterogeneous photocatalysis,26 since hydroxyl, superoxide and hydroperoxyl radicals are recognized oxidizing species in photocatalytic degradation processes 26–28. Thus, our proposals for 4′‐nitro‐4‐biphenylamine, 4,4′‐dinitrobiphenyl and tetrahydroxybiphenyl as benzidine degradation products are feasible.…”

Section: Resultsmentioning

confidence: 99%

Benzidine photodegradation: a mass spectrometry and UV spectroscopy combined study

Madeira¹,

Nunes²,

Borges³

et al. 2005

Rapid Comm Mass Spectrometry

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The benzidine photodegradation process was studied using UV/Vis spectroscopy and electrospray ionization mass spectrometry (ESI-MS) combined with collision-induced dissociation (CID) and tandem mass spectrometry (MS/MS). Mass spectrometry was used to characterize benzidine and to identify and characterize possible degradation products and intermediates. The MS data showed that benzidine is quite persistent in aqueous medium. Moreover, the MS analysis enabled us to propose the following three degradation products/intermediates: 4 0 -nitro-4-biphenylamine, tetrahydroxybiphenyl and 4,4 0 -dinitrobiphenyl. For the benzidine molecular ion and protonated molecule and for the protonated molecules of the degradation products/intermediates detected, fragmentation patterns are proposed based on CID and MS/MS data. For the photodegradation process different catalysts were used, namely the commercial TiO 2 Degussa P25, and the laboratory-prepared ZnO, TiO 2 anatase and a titanium-zinc oxide with a perovskite type structure. Comparison of the different catalysts showed that degradation was favoured with the commercial TiO 2 . Nevertheless, the other catalysts appear to be promising and economic alternatives for potential future remediation studies.

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“…Indeed, the synthetic strategies for the generation of nitrile oxides are diverse: The reactive 1,3‐dipole is accessible via the dehydration of primary nitro compounds employing either phenyl isocyanates (Mukaiyama procedure) or ethyl chloroformate (Shimizu method), or by a halogenation‐dehydrohalogenation process of aldoximes . However, harsh conditions in terms of strong bases, e. g. alkali hydroxides, and high temperatures are often required, or potential hazardous metal complexes are employed . With these challenges in mind, we introduce a light‐driven mild alternative for nitrile oxide generation utilizing pyrene as a chromophore, hence making the access to isoxazolines and isoxazoles substantially more efficient (refer to Scheme and Scheme S1 in the Supporting Information).…”

Section: Methodsmentioning

confidence: 98%

Pyrene‐Tagged Chloro Oximes as Ambient‐Light‐Accelerated Ligation Agents

et al. 2018

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We demonstrate how a normally base‐induced or transition‐metal‐catalyzed cycloaddition reaction can be executed without additives by equipping the reactant with a chromophore as a light‐harvesting unit, able to exploit light to boost the reaction. Specifically, we generate a highly reactive nitrile oxide upon light irradiation which is able to undergo cycloaddition reactions with a wide range of substrates by introducing a pyrene unit into the oxime precursor. Commercially available LED setups, and even ambient light, were successfully employed to induce the cycloaddition. Our approach demonstrates that the careful design of light‐harvesting chromophores can be a powerful tool to facilitate light‐induced chemical transformations.

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Nitro and related groups

Cited by 64 publications

References 122 publications

Flavin‐Catalyzed Oxidation of Amines and Sulfides with Molecular Oxygen: Biomimetic Green Oxidation

Flavin‐Catalyzed Oxidation of Amines and Sulfides with Molecular Oxygen: Biomimetic Green Oxidation

Benzidine photodegradation: a mass spectrometry and UV spectroscopy combined study

Pyrene‐Tagged Chloro Oximes as Ambient‐Light‐Accelerated Ligation Agents

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