101-63-3Relevant articles and documents
Microwave-assisted construction of diaryl ethers directly from arylmethanesulfonates as convenient latent phenols with aryl halides
Xu, Hui,Chen, Yang
, p. 2411 - 2420 (2007)
The microwave-assisted synthesis of diaryl ethers directly from aryl halides and arylmethanesulfonates, which as latent phenols obviate a deprotection step prior to the SNAr reaction, in the presence of Cs2CO3 is described. The reaction time was very short (6-9-min), and good to excellent yields (53-90%) with the wide substrate scope were achieved without any catalyst. Copyright Taylor & Francis Group, LLC.
Eyring Activation Barriers for the Anomalous Dielectric Relaxations of Diphenyl Ether Type Molecules
Chao, J.,Desando, M. A.,Gourlay, D. L.,Orr, D. E.,Walker, S.
, p. 711 - 716 (1984)
Several symmetrically substituted diaryl ethers have been studied in a polystyrene matrix and bis(4-nitrophenyl) ether also in glassy o-terphenyl by dielectric adsorption techniques in the frequency range 10-1E5 Hz over temperatures of 77-323 K.Bis(4-cyanophenyl) ether in polystyrene was also examined at many temperatures in the frequency range E-4-E-7Hz.In the polystyrene matrix both the molecular and intramolecular relaxation processes were detected for diphenyl ether and bis(4-nitrophenyl) ether.An intramolecular relaxation process was detected for most of the aromatic ethers, and the associated Eyring enthalpy of activation is ca. 10 kJ mol-1.Which is similar to that observed for some alkyl aryl ethers in the same media.The present work establishes that the energy barrier for rotation around the C-O bonds is symmetrically substituted diphenyl ethers is very low and that intramolecular motion would be expected to occur quite readily about these bonds.
A PEG1000-DAIL[CdCl3]-toluene temperature-dependent biphasic system that regulates homogeneously catalyzed C-O coupling of organic halides with phenols and alcohols under ligand-free conditions
Hu, Yu Lin,Ma, Xiao Yun,Lu, Ming
, p. 471 - 480 (2011)
An efficient, experimentally simple, and convenient procedure for the C-O coupling of organic halides with phenols and alcohols in a PEG 1000-DAIL[CdCl3]-toluene temperature-dependent biphasic system has been developed. The product can be easily isolated by a simple decantation, and the catalytic system can be recycled and reused without loss of catalytic activity.
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Haeussermann,Teichmann
, p. 1449 (1896)
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Ultrasound synthesis of diaryl ethers
Begunov,Valyaeva,Belyaev,Dobretsova
, p. 1971 - 1974 (2015)
2,2-Bis[4-(4-nitroaryl)phenyl]hexafluoropropanes appropriate for the synthesis of monomers were prepared by the reaction of 2,2-bis[4-hydroxyphenyl)hexafluoropropane with 1-chloro-4-nitrobenzenes under ultrasonic activation.
Synthesis of diaryl ethers, diaryl sulfides, heteroaryl ethers and heteroaryl sulfides under microwave dielectric heating
Li, Feng,Meng, Qingqing,Chen, Huansheng,Li, Zhiming,Wang, Quanrui,Tao, Fenggang
, p. 1305 - 1313 (2005)
This paper describes the synthesis of diaryl ethers and sulfides by utilizing microwave heating methodology. The methodology is shown to be rapid and efficient for the coupling of phenols or thiophenol with electron-deficient aryl halides through a SNAr reaction. The scope of the protocol can be expanded to six-membered heterocycles bearing a hydroxyl group as well as to the reaction of 2-pyrimidinethiol with mildly activated aryl halides, providing heteroaryl ethers and sulfides, respectively. The advantages of the present method include the wide substrate scope, the obviation of metal catalysts, ease of product isolation, and high purity of products. Georg Thieme Verlag Stuttgart.
Visible-light-mediated synthesis of diaryl ethers from arylboronic acids and diaryliodonium salts
Liu, Li,Tang, Jiaqi,Qiang, Jian,Li, Jian,He, Mingyang
, p. 261 - 264 (2016)
With visible-light irradiation, a simple and metal-free photocatalytic system for the synthesis of diaryl ethers from arylboronic acids and diaryliodonium salts has been developed. The reaction proceeded in high yield for a range of different substrates in the presence of eosin Y under mild reaction conditions.
CsF/clinoptilolite: An efficient solid base in SNAr and copper-catalyzed Ullmann reactions
Keipour, Hoda,Hosseini, Abolfazl,Afsari, Amir,Oladee, Razieh,Khalilzadeh, Mohammad A.,Ollevier, Thierry
, p. 95 - 104 (2015)
CsF/clinoptilolite was found to be an efficient solid base catalyst for both SNAr and Ullmann ether reactions. A general and efficient one-step procedure was developed for the synthesis of biaryl ethers via direct coupling of electron-deficient aryl halides to phenols using CsF/clinoptilolite. The protocol was also applied to electron-rich aryl halides by addition of a catalytic amount of copper oxide nanoparticles. Both SNAr and Ullmann reactions were rapid and provided good to excellent yields.
Synthesis of copper nanoparticles supported on a microporous covalent triazine polymer: An efficient and reusable catalyst for O-arylation reaction
Puthiaraj, Pillaiyar,Ahn, Wha-Seung
, p. 1701 - 1709 (2016)
Copper nanoparticles were supported on a microporous covalent triazine polymer prepared by the Friedel-Crafts reaction (Cu@MCTP-1). The resulting material was characterized by powder X-ray diffraction, thermogravimetric analysis, N2 adsorption-desorption isotherms at 77 K, transmission electron microscopy, X-ray photoelectron spectroscopy, and inductively coupled plasma optical emission spectroscopy, and Cu particles with an average size of 3.0 nm and a BET total surface area of ca. 1002 m2 g-1 were obtained. Cu@MCTP-1 was evaluated as a heterogeneous catalyst for the Ullmann coupling of O-arylation over a series of aryl halides and phenols without employing expensive ligands or inert atmosphere, which produced an excellent yield of the corresponding diaryl ethers. The catalyst could be recovered by simple centrifugation and was reusable at least five times with only a slight decrease in catalytic activity.
Bis(aniline) compounds containing multiple substituents with carbon-carbon triple-bonded groups
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Sheet 1, (2021/04/28)
The invention relates to bis(aniline) compounds containing multiple arylethynyl, alkylethynyl, ethynyl groups or their combinations, processes of making such compounds and materials comprising such compounds. Such, bis(aniline) compounds preferably comprise multiple phenylethynyl (PE) groups, i.e. 2-4 PE moieties. Such compounds are useful monomers for the preparation of polyimides, polyamides and poly(amide-imides) whose post-fabrication crosslinking chemistry (i.e. reaction temperature) can be controlled by the number of PE per repeat unit as well as finding utility in thermosetting matrix resins, 3D printable resins, and as high-carbon-content precursors to carbon-carbon composites.
Synthesis method of 4, 4-amino diphenyl ether
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Paragraph 0005; 0009; 0034-0044, (2020/12/30)
The invention discloses a synthesis method for synthesizing 4, 4-amino diphenyl ether in a water phase, and belongs to the field of organic synthesis. The method comprises the following steps: adding4-nitrochlorobenzene into water, adding potassium hydroxide and tetrabutylammonium bromide, and heating to react to obtain the 4, 4-nitrodiphenyl ether; and adding 4, 4-nitro diphenyl ether into water, adding hydrochloric acid and palladium on carbon, introducing hydrogen, and heating to react to obtain 4, 4-amino diphenyl ether. The method is easy and convenient to operate, no organic solvent isintroduced in the production process, the method is environmentally friendly, the yield of the obtained product is high, and the method is more suitable for large-scale production.
