- Synthesis method of high-purity phloroglucinol compound
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The invention discloses a one-step chemical catalytic synthesis method of high-purity phloroglucinol by taking 3,5-dichlorophenol as a starting material and taking strong base and a catalyst as auxiliary materials. Through the method, the phloroglucinol compound with high molar yield, high purity and low cost can be effectively synthesized.
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- Oxidative bromination of non-activated aromatic compounds with AlBr3/KNO3 mixture
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Bromination of non-activated aromatic compounds with reaction mixture containing KNO3 and AlBr3 was studied in liquid substrates and in solvent. Aluminium bromide has three different roles in this reaction mixture. First, it is a source of bromide ions, which are essential in oxidative bromination application. Second, it acts as a catalyst, and lastly, it forms acidic environment via its hydrolysis, which is necessary for enhancement of the oxidising properties of nitrate ions. It was shown that when changing the reaction conditions, different side reactions (like nitration or Friedel–Crafts type arylation) can occur. However, it is possible to guide the reaction path and receive the desired outcome by choosing the suitable reaction conditions. In addition, it was shown that there has to be water content in this reaction mixture as the bromine formation rate depends on it, while there exists an optimal volume of water, where bromine formation is the fastest.
- Rahu, Ida,J?rv, Jaak
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p. 1219 - 1227
(2019/11/13)
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- An alternative synthesis of 2,6-dimethoxyl-1,4-benzoquinone
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An economic four-step synthesis of 2,6-dimethoxy-1,4-benzoquinone was achieved in 68 % overall yield starting from aniline. The reaction sequence involved conversion to1,3,5-tribromoaniline, deamination, methoxylation, and oxidation. The procedure is operationally simple and amenable to scale-up production.
- Wang, Qian,Yang, Jian,Zheng, Yang,Liao, Xiali
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p. 193 - 194
(2017/06/20)
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- PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES
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The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.
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Paragraph 00139; 00141
(2017/07/28)
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- COMPOUND FOR ORGANIC ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE INCLUDING THE SAME
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This invention relates to a compound for an organic electroluminescent device and to an organic electroluminescent device including the same. This compound for an organic electroluminescent device including the same is improved in thermal stability and light emission efficiency. When this compound is used as a hole transport layer material, a triplet energy of a phosphorescent light emitting material is increased, thus improving the efficiency of the organic electroluminescent device.
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- Trigonal rigid triphenols: Self-assembly and multicomponent lattice inclusion
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The sterics introduced via methyl groups impart rigidity and inclusion behavior to trigonal C3-symmetric triphenol hosts H1-H4. Triphenol H1 is found to mimic the O-H...O hydrogen-bonded self-assembly of trimesic acid to yield porous honeycomb nets. It is found that 18-crown-6?H1 in turn binds guest molecules in the hexagonal voids to yield guest?guest?host multicomponent molecular crystals. The triphenol H2 and the homologous derivatives H3 and H4 are also found to crystallize with 18-crown-6 and other guests to yield multicomponent crystals, but in these cases the 18-crown-6 is found to serve as a spacer. While the structure of H2 is determined in its guest-free form, some of the inclusion compounds of triphenols lend themselves to crystal packings that are deciphered based on network topologies. The networks observed for H1-Tol and H3-C-B-Et are unique; in the latter, the crystal packing analysis reveals organization of molecules into a pattern that is reminiscent of borromean rings.
- Moorthy, Jarugu Narasimha,Natarajan, Palani,Bajpai, Alankriti,Venugopalan, Paloth
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scheme or table
p. 3406 - 3417
(2012/04/04)
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- Synthesis of poly-nitrile aromatics via palladium-catalyzed cyanation of aryl bromides with potassium hexacyanoferrate(II)
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(Chemical Equation Presented) Modification of Beller's palladium-catalyzed cyanation procedure leads to a versatile and rapid route to poly-nitrile aromatics via easily available aryl bromides that improve on known literature methods. All cyanide ions on the iron(II) center of the non-toxic cyanide source [potassium hexacyanoferrate(II)] can be transferred to the aryl halide using palladium(II) acetate and 1,1′-bis(diphenylphosphino)ferrocen (dppf). Copyright Taylor & Francis Group, LLC.
- Becker, Martin,Schulz, Axel,Voss, Karsten
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experimental part
p. 1042 - 1051
(2011/05/06)
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- Hydrodediazoniation of dry arenediazonium o-benzenedisulfonimides with hydrogen peroxide
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This report describes the hydrodediazoniation of dry arenediazonium o-benzenedisulfonimides 1 with hydrogen peroxide (2) in THF at reflux. The new procedure is general, giving positive results in the presence of both electron-donating and electron-withdrawing substituents. Furthermore, it does not suffer from steric effects and always gives the pure reduction products 3 in excellent yields (15 examples, average yield = 93%). All the reactions show over 90% recovery of o-benzenedisulfonimide (4) that can be reused to prepare the salts 1. The collateral proofs we performed led us to hypothesize, for this reaction, a free-radical chain mechanism in which 2 is the exclusive hydrogen source in the arenes Ar-H 3.
- Barbero, Margherita,Degani, Iacopo,Dughera, Stefano,Fochi, Rita
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p. 2386 - 2390
(2007/10/03)
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- Buttressing Effects Rerouting the Deprotonation and Functionalization of 1,3-Dichloro- and 1,3-Dibromobenzene
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A systematic comparison between 1,3-difluorobenzene, 1,3-dichlorobenzene, and 1,3-dibromobenzene did not reveal major differences in their behavior towards strong bases such as lithium diisopropylamide or lithium 2,2,6,6-tetramethyl-piperidide. Thus, all 2,6-dihalobenzoic acids 1 are directly accessible by consecutive treatment with a suitable base and dry ice. In contrast, (2,6-dichlorophenyl)- and (2,6-bromo-phenyl)triethylsilane (2a and 2b) were found to undergo deprotonation at the 5-position (affording acids 3 and, after deprotection, 4), whereas the 1,3-difluoro analog is known to react at the 4-position. The 2,4-dihalobenzoic acids 7 were selectively prepared from either the silanes 2 (by bromination at the 4-position, metalation and carboxylation of the neighboring position, followed by desilylation and debromination) or the 1,3-dihalo-2-iodobenzenes 8 (by base-promoted migration of iodine to the 4-position followed by iodine/magnesium permutation and subsequent carboxylation). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Heiss, Christophe,Marzi, Elena,Schlosser, Manfred
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p. 4625 - 4629
(2007/10/03)
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- Fluorodediazoniation in ionic liquid solvents: New life for the Balz-Schiemann reaction
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Drawbacks associated with the classic Balz-Schiemann reaction are eliminated in a series of examples by conducting fluorodediazoniation in ionic liquid solvents, thus opening up a new horizon for a much in demand process.
- Laali, Kenneth K.,Gettwert, Volker J.
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- 1-Aryl-3,3-dialkyltriazenes: A convenient synthesis from dry arenediazonium o-benzenedisulfonimides - A high yield break down to the starting dry salts and efficient conversions to aryl iodides, bromides and chlorides
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This research comprises three parts. The first part regards the synthesis of 1-aryl-3,3-dialkyltriazenes 3 by reaction of dry arenediazonium o-benzenedisulfonimides 1, also coming from weakly basic aromatic amines with dimethylamine or diethylamine in aqueous solution at 0-5 °C. Yields were usually greater than 90% and there was the possibility of recovering the o-benzenedisulfonimide (5), which could be reused to prepare the salts 1. In the second part it was demonstrated that there is the possibility of reconverting the triazenes 3 into the starting stable dry salts 1 by using 5 as acid. The reactions were carried out in glacial acetic acid at 50-55 °C and normally afforded salts 1 in yields of around 90-99%. The third part concerns the setting up of two procedures for the conversion of 3 to aryl iodides 9, bromides 10 and chlorides 11. Procedure A used the corresponding aqueous hydrogen halides in acetonitrile at r.t. or 60 °C, sometimes in the presence of aqueous HBF4, sometimes Cu powder (25 examples, yields 65%-88%). Procedure B usually used anhydrous methanesulfonic acid and tetraalkylammonium halides in anhydrous acetonitrile at temperatures varying from r.t. to 80 °C, sometimes in the presence of Cu (16 examples, yields 65-88%).
- Barbero,Degani,Diulgheroff,Dughera,Fochi
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p. 2180 - 2190
(2007/10/03)
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- Aprotic diazotization in the presence of cuprous cyanide
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In a procedure of extreme simplicity and rapidity a mixture of an aromatic primary amine, copper (I) cyanide and an alkyl nitrite in dimethyl sulphoxide yielded fair to moderate yields of the corresponding nitriles. Side processes observed were reduction (NH2&[H), nitration (NH2←NO2) and hydroxylation (NH2&[OH). In the case of polyhaloanilines halogen dance products could be detected.
- Giumanini, Angelo G.,Verardo, Giancarlo,Geatti, Paola,Strazzolini, Paolo
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p. 7137 - 7148
(2007/10/03)
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- Efficient Catalysis of Hydrodediazoniations in Dimethylformamide
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For hydrodediazoniations (the replacement of a diazo group by hydrogen) in DMF, several substances act as catalysts through their ability to serve as electron donors and initiate free-radical reactions.A general procedure has been developed in which FeSO4 speeds the conversion and leads to higher yields.Trapping experiments demonstrated the presence of free-radical intermediates.N,N-Dimethylacetamide was found to rival DMF as a source of hydrogen atoms.
- Wassmundt, Frederick W.,Kiesman, William F.
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p. 1713 - 1719
(2007/10/02)
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- 27. Magnetic-Field Effect in Aromatic Dediazoniation
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Homolytic dediazoniation of tribromo- and trichloro-benzenediazonium tetrafluoroborates in highly ionizing, low-nucleophilicity solvents (trifluoroethanol and trifluoromethanesulfonic acid (TfOH)) exhibits a strong magnetic-field dependency of dediazoniation products; a more facile singlet-to-triplet intersystem crossing results in increased radical-escape products at higher magnetic fields.
- Laali, Kenneth K.,Gao, Hong
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p. 304 - 308
(2007/10/02)
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- Magnetic susceptibilities of organic compounds: Part V - Influence of substituents on diamagnetic susceptibilities of disubstituted and trisubstituted benzenes
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The magnetic susceptibilities of a number of triads of isomeric disubstituted benzenes have been determined, choosing the compounds in such a way that the substituents are present in the following combinations: (i) two electron-releasing substituents, (ii) a halogeno and an electron-releasing substituent, (iii) a halogeno and an electron-attracting substituent, and (iv) two halogeno substituents.The data show that for types (i), (ii) and (iv), the ortho isomers have the highest magnetic susceptibilities, the susceptibilities decreasing in the order: ortho > meta > para; for type (iii), the meta-isomers have the highest susceptibilities, the susceptibilities decreasing in the order: meta > para > ortho.The diamagnetic susceptibilities of some isomeric trisubstituted benzenes have also been determined and the data reveal that the susceptibility is the highest where the crowding of substituents is the highest (1,2,3-isomer) and lowest where the substituents are staggered and least crowded (1,3,5-isomer).Another observation made in the case of trisubstituted benzene is the applicability of a principle of additivity of their diamagnetic susceptibilities.
- Baliah, V.,Jeyanthy, J. Judith Diana
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p. 472 - 476
(2007/10/02)
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- Selective Reactions in the Triazene Series. Part 2. Protodediazoniation of Arenediazonium Salts with Formamide
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Treatment of performed arenediazonium tetrafluoroborates or arenediazonium trifluoroacetates (formed in situ) with formamide an base effects reduction to the corresponding arene in moderate to good yield in cases where an electron-withdrawing substituent is present on the aromatic ring.Other functionalities remain unaffected.The mechanism of the protodediazoniation is shown to involve transfer of the formyl hydrogen atom to the substrate and may proceed via a 1-aryl-3-formyltriazine.
- Threadgill, Michael D.,Gledhill, Adrian P.
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p. 873 - 876
(2007/10/02)
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- Homosolvolysis
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Nitroxides, when used as solvents, promote the homolysis of a variety of weak bonds.Strong chemical evidence for the formation of free radicals is confirmed by e.s.r. studies in which the formation of free radicals has been monitored.This fission of single bonds of solute molecules dissolved in solvents with unpaired electrons is called homosolvolysis, in contrast to the common bond fission observed in polar solvents which is called heterosolvolysis.
- Scott, Alan C.,Tedder, John M.,Walton, John C.,Mhatre, Sushila
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p. 260 - 266
(2007/10/02)
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