10403-47-1Relevant articles and documents
Effect of Hydrogen Bond on Second-Order Nonlinear Optical Property of 2-Alkylcarboxamido-4′-methoxy-4-nitrotolan Derivatives
Kato, Midori,Okunaka, Masaaki,Sugita, Nami,Kiguchi, Masashi,Taniguchi, Yoshio
, p. 583 - 585 (1997)
We have synthesized a series of 2-alkylcarboxamido-4′-methoxy-4-nitrotolan derivatives and studied the second-order nonlinear optical properties using the total reflection technique. We measured the infrared absorption spectra of the derivatives and examined the absorption peak of the N-H stretching vibration around 3300 cm-1, which is sensitive to hydrogen bonding. We observed that the peak frequencies of the nonlinear optical active materials were lower than those of the inactive ones, and thus found that for 2-alkylcarboxamido-4′-methoxy-4-nitrotolan derivatives the hydrogen bond plays an important role in activating the second-order optical nonlinearity of the material.
Factors controlling regioselectivity in the reduction of polynitroaromatics in aqueous solution
Barrows, Susan E.,Cramer, Christopher J.,Truhlar, Donald G.,Elovitz, Michael S.,Weber, Eric J.
, p. 3028 - 3038 (1996)
Regioselectivities in the bisulfide reduction of 10 polynitroaromatics (PNAs) to monoamine products have been determined; four of these compounds have also been reduced by anoxic sediments in heterogeneous aqueous solution, and the same regioselectivities are observed. Analyses of Austin Model 1- Solvation Model 2 electrostatic potential surfaces for the radical anions of these polynitroaromatic compounds provides a reliable method of predicting the regioselectivity of their reduction. In particular, at their minimum- energy geometries in aqueous solution, it is the more negative nitro group that is selectively reduced. This is consistent with a mechanism where regioselection occurs upon kinetic protonation at the site of maximum negative charge in the radical anion formed after the first electron transfer to the neutral PNA. Inclusion of solvation effects is critical in order to confidently predict the electrostatic preference for the reduction of one nitro group over the others. Sterically uncongested nitroaromatic radical anions have gas-phase geometries in which the nitro group is coplanar with the aromatic ring. However, ortho substituents and solvation effects both oppose this tendency and can lead to nitro groups that are rotated out of the ring plane and pyramidalized.
Cu-mediated selective bromination of aniline derivatives and preliminary mechanism study
Zhao, Hong-Yi,Yang, Xue-Yan,Lei, Hao,Xin, Minhang,Zhang, San-Qi
supporting information, p. 1406 - 1415 (2019/05/01)
A simple and efficient bromination of aniline, aniline derivatives, and analogs have been developed. Forty three examples were given and the highest yield reached was 98%. Different substrates including substituted aniline, pyridin-amine, N-substituted aniline, N,N-disubstituted aniline, N-phenyl-amide, N-phenyl-sulfonamide, and nitrogen-containing heterocycles were all reactive and selectively generated desired bromo-products. The method can be applied to synthesize drug intermediate and quinoxaline derivatives.
Iridium-catalyzed intramolecular C–N and C–O/S cross-coupling reactions: Preparation of benzoazole derivatives
Shi, Yajie,Zhou, Qifan,Du, Fangyu,Fu, Yang,Du, Yang,Fang, Ting,Chen, Guoliang
supporting information, (2019/09/10)
The irdium-catalyzed intramolecular arylcarbon-hetero cross-coupling reactions with o-haloarylamides or o-haloarylamidine have been effectively achieved using KOAc and just 1 mol% catalyst. The [Ir(cod)Cl]2 was proved to be more potential for smoothly assembling functional structures benzimidazoles, benzoxazoles and benzothiazoles, which was superior to Cu- and Pd-catalyzed systems. Simultaneously, a concise and efficient synthesis of tafamidis was developed in 5-g scale.
Polymer-anchored peroxo compounds of molybdenum and tungsten as efficient and versatile catalysts for mild oxidative bromination
Boruah, Jeena Jyoti,Das, Siva Prasad,Borah, Rupam,Gogoi, Sandhya Rani,Islam, Nashreen S.
, p. 246 - 254 (2013/05/23)
A polymer supported peroxomolybdate(VI) compound of the type [MoO 2(O2)(CN)2]-PAN [PAN = poly(acrylonitrile)] (PANMo) was obtained by reacting H2MoO4 with 30% H 2O2 and the macromolecular ligand, PAN at near neutral pH. The macrocomplex has been characterized by elemental analysis (CHN and EDX analysis), spectral (IR, UV-Vis and 13C NMR, 95Mo NMR), thermal (TGA-DTG) as well as SEM studies. The catalytic activity of PANMo and its previously reported tungsten containing analog PANW, in oxidative bromination of organic substrates has been explored. The supported complexes could serve as efficient heterogeneous catalysts for the oxidative bromination of a variety of structurally diverse aromatic compounds, with H 2O2 as terminal oxidant, to afford bromo organics in impressive yields under environmentally clean conditions. The catalysts afforded regeneration and could be reused for a minimum of six reaction cycles.
Electrophilic bromination of meta-substituted anilines with N-bromosuccinimide: Regioselectivity and solvent effect
Bartoli, Sandra,Cipollone, Amalia,Squarcia, Antonella,Madami, Andrea,Fattori, Daniela
experimental part, p. 1305 - 1308 (2009/12/24)
N-Bromosuccinimide-mediated electrophilic aromatic bromination of a series of anilines substituted with an electron-with-drawing group in the meta position was investigated. The regioselectivity of the reaction is markedly dependent on the polarity of the solvent and the bromination reaction can be tuned by appropriate selection of the reaction medium. Georg Thieme Verlag Stuttgart.
Effect of the electronic structure of the radical anions of 4-substituted 1,2-and 1,3-dinitrobenzenes on the regioselectivity of reduction of the nitro groups
Orlov,Begunov,Demidova,Rusakov
, p. 76 - 81 (2007/10/03)
Theoretical and experimental regularities of the regioselectivity of the reduction of one of the two nitro groups in unsymmetrical dinitrobenzenes were studied. It was found that the regioselectivity of the formation of isomeric nitroanilines depends on the structure of the substrate and the nature of the reducing agent. The reduction regioselectivity model was verified, according to which radical anion protonation is the major reaction direction. Pleiades Publishing, Inc. 2006.
