- Steric-Hindrance-Induced Regio- and Chemoselective Oxidation of Aromatic Amines
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Unusual regio- and chemoselective oxidation of aromatic amines hindered with ortho substituents (except -NH2, -NHCH3, and -OH) to the corresponding nitro compounds is described by use of nonanebis(peroxoic acid). The mechanistic investigation for selective oxidation of amines ortho-substituted with -NH2 or -OH showed the involvement of H-bonding between the ortho hydrogen of the adjacent -XH group (where X = NH, NR, or O) and an oxygen atom from the diperoxy acid. Various mono- and diamines are oxidized into corresponding mononitro derivatives in high yield and purity without employing any protection strategies. The protocol was also found to successful on the gram scale.
- Patil, Vilas Venunath,Shankarling, Ganapati Subray
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p. 7876 - 7883
(2015/09/01)
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- Nanoscale Fe2O3-based catalysts for selective hydrogenation of nitroarenes to anilines
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Production of anilines - key intermediates for the fine chemical, agrochemical, and pharmaceutical industries - relies on precious metal catalysts that selectively hydrogenate aryl nitro groups in the presence of other easily reducible functionalities. Herein, we report convenient and stable iron oxide (Fe2O3) - based catalysts as a more earth-abundant alternative for this transformation. Pyrolysis of iron-phenanthroline complexes on carbon furnishes a unique structure in which the active Fe2O 3 particles are surrounded by a nitrogen-doped carbon layer. Highly selective hydrogenation of numerous structurally diverse nitroarenes (more than 80 examples) proceeded in good to excellent yield under industrially viable conditions.
- Jagadeesh, Rajenahally V.,Surkus, Annette-Enrica,Junge, Henrik,Pohl, Marga-Martina,Radnik, Joerg,Rabeah, Jabor,Huan, Heming,Schunemann, Volker,Brueckner, Angelika,Beller, Matthias
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p. 1073 - 1076
(2014/01/06)
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- The conversion of 2-(4-chloro-5H-1,2,3-dithiazolylideneamino)benzonitriles into 3-aminoindole-2-carbonitriles using triphenylphosphine
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2-(4-Chloro-5H-1,2,3-dithiazolylideneamino)benzonitrile 1a reacts with triphenylphosphine (4 equiv) in the presence of water (2 equiv) to afford anthranilonitrile 2a, 3-aminoindole-2-carbonitrile 3a and (2-cyanoindol-3-yl)iminotriphenylphosphorane 4a, tog
- Michaelidou, Sophia S.,Koutentis, Panayiotis A.
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experimental part
p. 8428 - 8433
(2009/12/26)
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- Synthesis and Spectral Characterization of Blue Dyes of the Benzene Series
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53 Donor-acceptor substituted azo dyes of the benzene series were prepared by diazonium-coupling reactions (1a-s) or halogen-cyanide exchange (->2a-x, 3a-j).Described are the preparation of the amines 4a-m and the coupling compounds 5a-t and the procedure of diazotizing and coupling.The colouristic and spectroscopic data show that compounds of the general formula 1 are excellent brilliant blue azo dyes usefull for dyeing polyester material.
- Thiel, W.,Mayer, R.,Jauer, E.-A.,Modrow, H.,Dost, H.
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p. 497 - 514
(2007/10/02)
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- Water-insoluble azo dyestuffs which are derivatives of 1-aryl-3-trifluoromethyl-5-pyrazolones
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Water-insoluble azo dyestuffs corresponding to the formula: STR1 in which X represents halogen, cyano, nitro, alkyl, polyfluoroalkyl, polyfluoroalkoxy, alkylsulphonyl, sulphonamido, or sulphonamido substituted by one or two alkyl groups; Y and Z are the same or different and represent hydrogen, halogen, cyano, nitro, alkyl, alkoxy, polyfluoroalkyl, polyfluoroalkoxy, alkylsulphonyl, sulphonamido or sulphonamidosubstituted by one or two alkyl groups; R represents hydrogen, halogen, cyano, nitro, alkyl, alkoxy, polyfluoroalkyl, polyfluoroalkoxy, alkylsulphonyl, sulphonamido, or sulphonamido substituted by one or two alkyl groups; m is equal to 0 or 1; and the nucleus A may be substituted by one or more chlorine atoms or alkyl, alkoxy or acylamino groups. These dyestuffs may be used for dyeing synthetic or artificial textile fibers, especially polyester fibers.
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- Navy-blue nitrophenylazonaphthylamino dyes
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Disperse monoazo dyes which are useful for the dyeing and printing of polyester fibers in navy-blue shades and which are of the formula: SPC1 Wherein R1 is halogen or CN; R2 is CN or NO2 ; R3 is alkylene; and n is 3 or 4; said dyes having good lightfastness and good hydrolytic stability.
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