87587-64-2Relevant academic research and scientific papers
Coupling of N -Nosylhydrazones with Nitrosoarenes: Transition-Metal-Free Approach to (Z)- N -Arylnitrones
Liu, Tingting,Liu, Zhaohong,Liu, Zhenhua,Hu, Donghua,Wang, Yeming
supporting information, p. 1728 - 1736 (2018/02/14)
An efficient and transition-metal-free protocol for the synthesis of (Z)- N -arylnitrones from the direct coupling of N -nosylhydrazones with nitrosoarenes under mild conditions is described. The protocol is compatible with a wide range of functional groups placed on both the reagents and provided the corresponding nitrones in good to excellent yields by simple recrystallization process. The use of these 1,3-dipoles for the synthesis of substituted indoles is elaborated for 2,3-diphenyl-1 H -indole.
Synthesis of Nitrosobenzene Derivatives via Nitrosodesilylation Reaction
Kohlmeyer, Corinna,Klüppel, Maike,Hilt, Gerhard
, p. 3915 - 3920 (2018/04/14)
The electrophilic ipso-substitution of trimethylsilyl-substituted benzene derivatives into nitrosobenzene derivatives is reported. The optimization of the reaction conditions was performed for moderately electron-deficient, electron-rich, and sterically hindered starting materials by varying reaction time, temperature, and equivalents of NOBF4. Also, a stable intermediate of the nitrosation reaction could be characterized by 19F NMR which can be assigned to a NO+ adduct with the nitrosobenzene derivative. This complex decomposes upon aqueous workup and liberates the desired nitrosobenzene derivative.
Titania-Supported Gold Nanoparticles Catalyze the Selective Oxidation of Amines into Nitroso Compounds in the Presence of Hydrogen Peroxide
Fountoulaki, Stella,Gkizis, Petros L.,Symeonidis, Theodoros S.,Kaminioti, Eleni,Karina, Athanasia,Tamiolakis, Ioannis,Armatas, Gerasimos S.,Lykakis, Ioannis N.
supporting information, p. 1500 - 1508 (2016/05/19)
In this article, the catalytic activity of titania-supported gold nanoparticles (Au/TiO2) was studied for the selective oxidation of amines into nitroso compounds using hydrogen peroxide (H2O2). Gold nanoparticles deposited on Degussa P25 polymorphs of titania (TiO2) have been found to promote the selective formation of a variety of nitroso arenes in high yields and selectivities, even in a large-scale synthesis. In contrast, alkyl amines are oxidized to the corresponding oximes under the examined conditions. Kinetic studies indicated that aryl amines substituted with electron-donating groups are oxidized faster than the corresponding amines bearing an electron-withdrawing functionality. A Hammett-type kinetic analysis of a range of para-X-substituted aryl amines implicates an electron transfer (ET) mechanism (ρ=-1.15) for oxidation reactions with concomitant formation of the corresponding N-aryl hydroxylamine as possible intermediate. We also show that the oxidation protocol of aryl amines in the presence of 1,3-cyclohexadiene leads in excellent yields to the corresponding hetero Diels-Alder adducts between the diene and the in situ formed nitrosoarenes.
Photosubstitution-photoreduction mechanistic duality in the SET photoreactions of nitrophenyl ethers with amines. The role of the steps that follow the ET
Mir, Miquel,Marquet, Jordi,Massot, Oriol
, p. 12603 - 12614 (2007/10/03)
Nitrophenyl ethers are photoreduced by primary amines in water through a mechanism initiated by single electron transfer that is in direct competition with the single electron transfer photosubstitution mechanism (S(N)Ar*-SET). Our results indicate that the preferred pathway does not depend on the electron donor or proton donor ability of the amine. The key factor that determines the progress of the photoreaction is the structure of the carbon skeleton of the amine, particularly the type of hydrogens on the carbon α to the amino group. A mechanistic rationale that includes hydrogen atom transfer as a key step is discussed.
Solid state photochemistry of ternary cyclodextrin complexes: Total selectivity in the photoreduction of nitrophenyl ethers by 1-phenylethylamine
Mir, Miquel,Marquet, Jorge,Cayon, Eduard
, p. 7053 - 7056 (2007/10/02)
The irradiation of the ternary complexes of β-cyclodextrin with several nitrophenyl ethers, and 1-phenylethylamine in the solid state, produces selective photoreduction to the corresponding nitroso derivatives.
Approaches to Azepines: A New Azepine by the Photolysis of Dimethyl p-Azidosalicylate
Mustill, Reginald A.,Rees, Alun H.
, p. 5041 - 5043 (2007/10/02)
We have generated 3-methoxy-4-carbomethoxyphenylnitrene and 3,4-dimethoxyphenylnitrene under various conditions, in a search for new azepines.Unexpectedly, only the former, by photolysis of dimethyl p-azidosalicylate, gave an azepine.Intramolecular coordi
