- Rh(II)-catalyzed intermolecular oxidative sulfamidation of aldehydes: A mild efficient synthesis of N-sulfonylcarboxamides
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Rh(II)-catalyzed oxidative coupling of aldehydes and sulfonamides has been developed to provide N-sulfonylcarboxamides in one step. A variety of sulfonamides were found to react with aromatic and aliphatic aldehydes to afford the desired products in good to excellent yields. Mechanistic data, including kinetic isotope effect experiments, suggest that the transformation proceeds through a concerted asynchronous nitrene insertion into an aldehydic hydrogen. Copyright
- Chan, Johann,Baucom, Kyle D.,Murry, Jerry A.
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- Bench-Stable Electrophilic Fluorinating Reagents for Highly Selective Mono- and Difluorination of Silyl Enol Ethers
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Efficient methods for the synthesis of fluorinated compounds have been intensively studied, recently. Development of practical fluorinating reagents is indispensable for this purpose. Herein, bench-stable electrophilic fluorinating reagents were synthesized as N-fluorobenzenesulfonimide (NFSI) substitutes. Reagents obtained by replacing one of the NFSI sulfonyl groups with an acyl group led to the highly selective monofluorination of silyl enol ethers with suppression of undesired overreaction, that is, difluorination. On the other hand, reagents bearing electron-withdrawing substituents at NFSI benzenesulfonyl groups efficiently facilitated the difluorination of silyl enol ethers under base-free conditions. Thus, both mono- and difluorinated target materials were prepared from the same substrate.
- Adachi, Akiya,Aikawa, Kohsuke,Ishibashi, Yuichiro,Nozaki, Kyoko,Okazoe, Takashi
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supporting information
p. 11919 - 11925
(2021/07/02)
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- A Novel C–N Migration Rearrangement Based on N–F Compounds for the Synthesis of N-Alkyl Diaryl Ureas
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A novel rearrangement reaction based on the structure of N-fluoro-N-(phenylsulfonyl) benzamides (FPSBA) was developed. In the presence of base, unsymmetrical N-alkyl diaryl ureas were obtained in good yields which were accomplished through secondary alkyl phenylamines initiated 1,2-phenyl-shift migration rearrangement of N-fluoro-N-(phenylsulfonyl) benzamides. The reaction was carried out without using traditional, highly toxic reagents and noble metals. Whereas without rearrangement occurrence for primary phenylamines and aliphatic amines, normal amides and N-(phenylsulfonyl) benzamides were afforded respectively. Nitrene and phenyl isocyanate included process were prevented and a secondary alkyl phenylamine initiated vicinal SN2' reaction occurred. This rearrangement reaction features an interesting reaction mechanism, mild reaction conditions, simple operation, and useful products.
- Zhao, Yi-Xiao,Xie, Tian,Yang, San-Ke,Yang, Xian-Jin
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p. 437 - 445
(2020/01/22)
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- Facile synthesis of acyl sulfonamides from carboxyic acids using the Mukaiyama reagent
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A fast and convenient method using the Mukaiyama reagent was developed to prepare acyl sulfonamides from carboxylic acids and sulfonamides. This methodology is effective for a range of acids and sulfonamides proceeding in moderate to good yields with the
- Chen, Ling,Luo, Guanglin
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supporting information
p. 268 - 271
(2019/01/04)
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- N-Sulfonyl acetylketenimine as a highly reactive intermediate for synthesis of N-Aroylsulfonamides
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A highly reactive intermediate N-sulfonyl acetylketenimine was generated from an ynone-participated CuAAC/ring-opening method. Its unique structure allowed it to react with aryl carboxylic acids to give N-aroylsulfonamides via a novel Mumm-type rearrangement.
- Yang, Weiguang,Huang, Dayun,Zeng, Xiaobao,Zhang, Jianlan,Wang, Xinyan,Hu, Yuefei
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p. 381 - 386
(2018/12/13)
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- Co-Catalyzed Synthesis of N-Sulfonylcarboxamides from Carboxylic Acids and Sulfonyl Azides
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A Co-catalyzed effective synthesis of N-sulfonylcarboxamides from the reaction of carboxylic acids and organic azides in the presence of isocyanide has been developed. The protocol has the advantages of short time, low temperature, and being oxidant-free, which provides a new and simple approach for the synthesis of N-sulfonylcarboxamides in good to excellent yields with a broad substrate scope.
- Fang, Yue,Gu, Zheng-Yang,Wang, Shun-Yi,Yang, Jin-Ming,Ji, Shun-Jun
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p. 9364 - 9369
(2018/07/09)
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- Ruthenium-Catalyzed Addition of Aromatic Amides to Internal Alkynes and Subsequent Intramolecular Cyclization for the Atom-Economical Synthesis of Isoindolinones
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A selective and atom-economical synthesis of isoindolinones is described. This novel synthetic strategy involves two catalytic reactions: the ruthenium-catalyzed regioselective alkenylation of aromatic C-H bond of aromatic amides with internal alkynes, an
- Miura, Hiroki,Terajima, Sachie,Tsutsui, Kentaro,Shishido, Tetsuya
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p. 1231 - 1239
(2018/06/18)
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- Catalytic activity of magnetic Fe3O4@Diatomite earth and acetic acid for the N-acylation of sulfonamides
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The Br?nsted and Lewis acidic promoted N-acylation of sulfonamides with acetic anhydride or benzoyl chloride has been achieved using glacial acetic acid and magnetic Fe3O4@Diatomite earth. Use of acetic acid as solvent omits the need for organic bases and permits the isolation of products by filtration and precipitation. Additionally, the magnetic composite Fe3O4@Diatomite acts as a conjugate proton super acid, enabling the acylation of sulfonamide compounds.
- Ghasemi, Mohammad Hadi,Kowsari, Elaheh,Hosseini, Seyed Kiumars
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supporting information
p. 387 - 391
(2016/01/12)
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- Acidylation method of amine
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The invention discloses an acidylation method of amine.The method includes the following steps that amine derivatives, hydrazide derivatives, organic peroxide and a catalyst are dissolved in a solvent and react at the temperature of 40-80 DEG C, and amide derivatives are obtained.The amide derivatives and hydrazide derivatives serve as initiators, the raw materials are easy to obtain and the number of varieties is large.Products obtained through the method are diverse in type, can be directly used and can also be used for other further reactions.The method is mild in reaction condition, simple in reaction operation and post-processing process, high in product yield and suitable for scale production.
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Paragraph 0036
(2016/10/10)
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- Iron-catalyzed kinetic resolution of N-sulfonyl oxaziridines
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We have developed a highly selective kinetic resolution of N-sulfonyl oxaziridines. This reaction utilizes an inexpensive and easily synthesized iron bis(oxazoline) catalyst to promote the efficient rearrangement of oxaziridines to the corresponding N-sulfonyl imides; no sacrificial reagents are required to effect this resolution. This process is readily translated to gram scale, which provides a practical method for the preparation of structurally diverse, enantiopure N-sulfonyl oxaziridines for use as reagents in organic synthesis.
- Williamson, Kevin S.,Sawicki, James W.,Yoon, Tehshik P.
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p. 3524 - 3527
(2014/08/18)
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- Iodide as an activating agent for acid chlorides in acylation reactions
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Acid chlorides can be activated using a simple iodide source to undergo nucleophilic attack from a variety of relatively weak nucleophiles. These include Friedel-Crafts acylation of N-methylpyrroles, N-acylation of sulfonamides, and acylation reactions of hindered phenol derivatives. The reaction is believed to proceed through a transient acid iodide intermediate.
- Wakeham, Russell J.,Taylor, James E.,Bull, Steven D.,Morris, James A.,Williams, Jonathan M. J.
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supporting information
p. 702 - 705
(2013/04/11)
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- ZnO and ZnO-nanoparticles: Efficient and reusable heterogeneous catalysts for one-pot synthesis of N-acylsulfonamides and sulfonate esters
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Commercially available and preparative ZnO nanoparticles are reported as efficient and reusable catalysts for the chemoselective synthesis of N-acylsulfonamides and sulfonate esters. A one-pot sequential sulfonylation and acylation of amines took place to afford the N-acylsulfonamides in excellent yields under solvent-free conditions. The ZnO catalyst can be reused for without significant loss of catalytic activity.
- Tamaddon, Fatemeh,Sabeti, Mohammad Reza,Jafari, Abbas Ali,Tirgir, Farhang,Keshavarz, Elham
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- Highly efficient one-pot synthesis of N-acylsulfonamides using cyanuric chloride at room temperature
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A highly efficient and very mild one-pot synthesis of N-acylsulfonamides is described using cyanuric chloride. In this synthesis, structurally diverse carboxylic acids and sulfonamides are reacted in the presence of cyanuric chloride, triethylamine, and alumina in anhydrous acetonitrile at room temperature to afford various N-acylsulfonamides in excellent yields. Georg Thieme Verlag Stuttgart New York.
- Soltani Rad, Mohammad Navid,Khalafi-Nezhad, Ali,Asrari, Zeinab,Behrouz, Somayeh
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experimental part
p. 2599 - 2603
(2010/09/07)
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- Synthesis, characterization, and antimicrobial evaluation of sulfonamides containing N-acyl moieties catalyzed by bismuth(III) salts under both solvent and solvent-free conditions
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Efficient N-acylation of sulfonamides with both readily available carboxylic acid chlorides and anhydrides has been carried out with catalysis by bismuth(III) salts including BiCl3 and Bi (OTf)3. The reactions proceed rapidly in both heterogeneous and solvent-free conditions and afforded the corresponding N-acylsulfonamides in good to excellent yields. The mild reaction conditions and low toxicity of bismuth salts make this procedure attractive and in close agreement with the goals of green chemistry. Some of the synthesized compounds were evaluated in vitro as antimicrobial agents against representative strains of Gram-positive (Staphylococcus aureus ATCC 25922, clinical strains of Staphylococcus aureus VISA and Enterococcus spp.) and Gram-negative bacteria (Pseudomonas aeruginosa ATCC 27853, clinical strains of Klebsiella pneumonia and Escherichia coli) and as antifungal agents against Candida albicans (clinically isolated) by both disc diffusion and minimal inhibition concentration (MIC) methods. All these bacteria and fungi studied were screened against some antibiotics to compare with our chemicals' zone diameters.
- Adibi, Hadi,Massah, Ahmad Reza,Majnooni, Mohammad Bagher,Shahidi, Sherita,Afshar, Maryam,Abiri, Ramin,Naghash, Hamid Javaherian
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experimental part
p. 2753 - 2766
(2010/10/21)
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- Molybdenum-mediated carbonylation of aryl halides with nucleophiles using microwave irradiation
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Figure Presented. A new, efficient, and practical molybdenum-mediated carbonylation of aryl and heteroaryl halides with a variety of nucleophiles is described using microwave irradiation. A range of reactions illustrating the wide scope of this chemistry were carried out and proceeded in good to excellent yields.
- Roberts, Bryan,Liptrot, David,Alcaraz, Lilian,Luker, Tim,Stocks, Michael J.
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supporting information; experimental part
p. 4280 - 4283
(2010/11/04)
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- HCIO4-SiO2 and NaHSO4-SiO2: Two efficient heterogeneous catalysts for synthesis of N-Acylsulfonamides under solvent-free conditions
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A simple and efficient synthesis of N-acylsulfonamides has been accomplished by the reaction of sulfonamides with anhydrides under solvent-free conditions in the presence of HClO4-SiO2 or NaHSO4-SiO2.copy;2009. Bentham Science Publis
- Liqiang, Wu,Chunguang, Yang,Chong, Zhang,Liming, Yang
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experimental part
p. 234 - 236
(2010/04/23)
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- A novel and efficient solvent-free and heterogeneous method for the synthesis of primary, secondary and bis-N-acylsulfonamides using metal hydrogen sulfate catalysts
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Some metal hydrogen sulfates were used as acid catalysts in the N-acylation of different sulfonamides using carboxylic acid chlorides and anhydrides as acylating agents under both heterogeneous and solvent-free conditions. Al(HSO4)3
- Massah, Ahmad Reza,Asadi, Beheshteh,Hoseinpour, Mahdieh,Molseghi, Azadeh,Kalbasi, Roozbeh Javad,Javaherian Naghash, Hamid
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experimental part
p. 7696 - 7705
(2009/12/04)
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- Development of an acyl sulfonamide anti-proliferative agent, ly573636 ? na
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The synthesis of 5-bromo-thiophene-2-sulfonic acid 2,4-dichlo- robenzoylamide sodium salt on multikilogram scale is described. The initial clinical supplies were made using carbonyl diimidazole to converge the two fragments. A more efficient acid chloride process has been developed, which also provides better control of impurities and color throughout the synthesis.
- Yates, Matthew H.,Kallman, Neil J.,Ley, Christopher P.,Wei, Jeffrey N.
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experimental part
p. 255 - 262
(2010/04/22)
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- Facile synthesis of N-acylsulfonamide in the presence of silica chloride (SiO2-Cl) both under heterogeneous and solvent-free conditions
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Sulfonamides were converted to the corresponding N-acyl sulfonamides with carboxylic acid chlorides and anhydrides in the presence of silica chloride. All reactions were performed in both heterogeneous and solvent-free conditions. This method provides the N-acyl sulfonamides products in good to high yield and purity. Copyright Taylor & Francis Group, LLC.
- Massah, Ahmad Reza,Momeni, Ahmad Reza,Dabagh, Mina,Aliyan, Hamid,Naghash, Hamid Javaherian
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p. 265 - 273
(2008/03/17)
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- Synthesis, in vitro antibacterial and carbonic anhydrase II inhibitory activities of N-acylsulfonamides using silica sulfuric acid as an efficient catalyst under both solvent-free and heterogeneous conditions
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Silica sulfuric acid catalyzes efficiently the reaction of sulfonamides with both carboxylic acid anhydrides and chlorides under solvent-free and heterogeneous conditions. All the reactions were done at room temperature and the N-acylsulfonamides were obtained with high yields and purity via an easy work-up procedure. This method is attractive and is in a close agreement with green chemistry. These compounds were also investigated for antibacterial activity, including Gram-positive cocci and Gram-negative bacilli, and carbonic anhydrase II inhibitory activity.
- Massah, Ahmad Reza,Adibi, Hadi,Khodarahmi, Reza,Abiri, Ramin,Majnooni, Mohammad Bagher,Shahidi, Sherita,Asadi, Beheshteh,Mehrabi, Masomeh,Zolfigol, Mohammad Ali
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p. 5465 - 5472
(2008/12/20)
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- An expeditious and convenient synthesis of acylsulfonamides utilizing polymer-supported reagents
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Acylsulfonamides can be rapidly and conveniently synthesized from a variety of carboxylic acids and sulfonamides utilizing the commercially available reagents, PS-DCC and DMAP under mild reaction conditions. DMAP can be efficiently scavenged by utilizatio
- Wang, Ying,Sarris, Kathy,Sauer, Daryl R.,Djuric, Stevan W.
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p. 5181 - 5184
(2008/02/08)
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- A new and efficient method for the facile synthesis of N-acyl sulfonamides under Lewis acid catalysis
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The N-acylation of sulfonamides with carboxylic acid anhydrides in the presence of Lewis acids is described. Several Lewis acids such as BF3·Et2O, ZnCl2, MoCl5, TiCl4, B(C6F5)su
- Raji Reddy, Chada,Mahipal, Bodugam,Yaragorla, Srinivasa Rao
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p. 7528 - 7532
(2008/03/14)
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- β-Keto sulfones as inhibitors of 11β-hydroxysteroid dehydrogenase type I and the mechanism of action
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The design, synthesis, and biological evaluation of β-keto sulfones as 11β-HSD1 inhibitors and the mechanism of inhibition are described here. This class of compounds is not active against 11β-HSD2 and therefore may have therapeutic potential for metabolic syndrome and type 2 diabetes.
- Xiang, Jason,Ipek, Manus,Suri, Vipin,Tam, May,Xing, Yuzhe,Huang, Nelson,Zhang, Yanling,Tobin, James,Mansour, Tarek S.,McKew, John
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p. 4396 - 4405
(2008/03/12)
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- Mechanism of thio acid/azide amidation
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A combined experimental and computational mechanistic study of amide formation from thio acids and azides is described. The data support two distinct mechanistic pathways dependent on the electronic character of the azide component. Relatively electron-rich azides undergo bimolecular coupling with thiocarboxylates via an anion-accelerated [3+2] cycloaddition to give a thiatriazoline. Highly electron-poor azides couple via bimolecular union of the terminal nitrogen of the azide with sulfur of the thiocarboxylate to give a linear adduct. Cyclization of this intermediate gives a thiatriazoline. Decomposition to amide is found to proceed via retro-[3+2] cycloaddition of the neutral thiatriazoline intermediates. Computational analysis (DFT, 6-31+G(d)) identified pathways by which both classes of azide undergo [3+2] cycloaddition with thio acid to give thiatriazoline intermediates, although these paths are higher in energy than the thiocarboxylate amidations. These studies also establish that the reaction profile of electron-poor azides is attributable to a prior capture mechanism followed by intramolecular acylation.
- Kolakowski, Robert V.,Shangguan, Ning,Sauers, Ronald R.,Williams, Lawrence J.
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p. 5695 - 5702
(2007/10/03)
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- Novel N-dealkylation of N-alkyl sulfonamides and N,N-dialkyl sulfonamides with periodic acid catalyzed by chromium(III) acetate hydroxide
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Chromium(III) acetate hydroxide has been found to be an efficient catalyst for N-dealkylation of N-alkyl sulfonamides and N,N-dialkyl sulfonamides to furnish sulfonamides in good to excellent yields with periodic acid in acetonitrile at room temperature.
- Xu, Liang,Zhang, Suhong,Trudell, Mark L.
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p. 1901 - 1904
(2007/10/03)
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- Novel polymer-supported coupling/dehydrating reagents for use in organic synthesis
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Two novel dehydrating reagents 3 and 4, based on a phosphonium anhydride and an oxyphosphonium triflate respectively, were prepared by reaction of the corresponding polymer-supported phosphine oxides with triflic anhydride. Reagent 3, based on the novel phosphorus heterocycle 1,1,3,3-tetraphenyl-2-oxa-1,3- diphospholanium bis(trifluoromethanesulfonate), was found to be a useful reagent for ester and amide formation. A wide range ofcoupling/dehydration-type reactions, such as ester, amide, anhydride, peptide, ether and nitrile formation, were performed in high yield using the more readily prepared polymer-supported triphenylphosphine ditrinate 4, which was easily recovered and re-used several times without loss of efficiency. With primary alcohols, both reagents 3 and 4 provide an alternative to the Mitsunobu reaction, where the use of azodicarboxylates and chromatography to remove the phosphine oxide by-product can be avoided. The use of 4-dimethylaminopyridine allowed the esterification of secondary alcohols with 4 to proceed in high yield but with retention of configuration.
- Fairfull-Smith, Kathryn E.,Jenkins, Ian D.,Longhlin, Wendy A.
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p. 1979 - 1986
(2007/10/03)
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- Fe-exchanged montmorillonite K10 - The first heterogeneous catalyst for acylation of sulfonamides with carboxylic acid anhydrides
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Fe-exchanged montmorillonite K10 catalyzes a highly efficient reaction between sterically and electronically diverse sulfonamides and carboxylic acid anhydrides to furnish N-acylsulfonamides in excellent yield and high selectivity. The catalyst can also be reused several times.
- Singh, Devendrapratap U.,Singh, Pankajkumar R.,Samant, Shriniwas D.
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p. 4805 - 4807
(2007/10/03)
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- Practical acid-catalyzed acylation of sulfonamides with carboxylic acid anhydrides
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A highly efficient reaction between sterically and electronically diverse sulfonamides and carboxylic acid anhydrides to furnish monoacylated N-acylsulfonamides is described. This represents the first systematic disclosure of the scope of sulfuric acid-ca
- Martin, Michael T.,Roschangar, Frank,Eaddy, John F.
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p. 5461 - 5463
(2007/10/03)
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- Solvent effects on the solvolyses of N-benzoyl-arenesulfonimidoyl chlorides
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Rates of solvolyses of N-benzoyl-arenesulfonimidoyl chlorides have been studied in different compositions of aqueous organic solvents and analysed in terms of the mol fraction of organic solvent, the dielectric constant, the Kirkwood function, the polarisibility, some ENT values, a multiparameter equation and the Grunwald-Winstein equation. All these criteria were consistent with a concerted bimolecular SN2 mechanism of solvolysis.
- Kutuk, Halil,Tillett, John G.
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- A convenient method for the preparation of acylsulfonamide libraries
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The preparation of an acylsulfonamide library is described using resin bound EDC (1-(3-dimethylaminopropyl)-3-ethylcarbodiimide). A polymer supported sulfonic acid (A-15) is used as a scavenger to remove dimethylaminopyridine and purification only involve
- Sturino, Claudio F.,Labelle, Marc
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p. 5891 - 5894
(2007/10/03)
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- A STUDY OF TRANSMISSION EFFECTS OF SULFONYL AND CARBONYL GROUPS
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Seventeen p-substituted N-phenylsulfonylbenzamides of general formulas XC6H4SO2NHCOC6H5 and C6H5SO2NHCOC6H4X have been synthesized and their structure has been confirmed by elemental analysis and 1H NMR spectra.The dissociation constants of all compounds have been measured by potentiometric titration in methanol, acetonitrile, dimethylformamide, dimethyl sulfoxide, and pyridine.The obtained pKHA values have been correlated with three sets of Hammett substituent constants using simple or double linear regression.The solvent and substituent effects are discussed on the basis of experimental results, and the difference between the substituent effects from sulfonamide and benzamide sections is evaluated.It has been found that due to extensive delocalization of negative charge in the conjugated base the transmission effects of carbonyl and sulfonyl groups on the transmission of substituent effect are roughly the same.The experimental data have been interpreted by the methods with latent variables: the principal component analysis (PCA), the conjugated deviation analysis (CDA), and the method of projection to latent structures (PLS).The results obtained by these procedures were similar.
- Ludwig, Miroslav,Parik, Patrik,Kulhanek, Jiri
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p. 841 - 850
(2007/10/02)
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- Footprint Catalysis. II. Molecular Recognition of Footprint Catalytic Sites
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In order to investigate the molecular recognition capability of "footprint" catalytic sites, the affinities of nine "footprint" catalysts for eleven competitive inhibitors, closely related to template molecules, were estimated through the competitive inhibition constants, Ki .An examination of the affinity revealed that the recognition by "footprint" catalytic sites was so highly specific that it could recognize not only the whole, but also the partial, stuctures of the bound molecules.
- Morihara, Kensaku,Nishihata, Emiko,Kojima, Mari,Miyake, Sayoko
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p. 3999 - 4004
(2007/10/02)
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- ALKALINE HYDROLYSIS AND AMINOLYSIS OF N-ACYL-ARENEIMINOSULPHONATE ESTERS
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A series of N-acylarenesulfonimidic aryl esters has been synthesised.These esters hydrolyse in alkali by a bimolecular nucleophilic substitution mechanism with essentially exclusive S-O cleavage, an interpretation supported by activation parameters, solve
- Said, Fouad M.,Douglas, Kenneth T.
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p. 361 - 370
(2007/10/02)
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- SYNTHESIS AND AROMATIZATION OF INDOLE DERIVATIVES OF N-IMIDOYLDIHYDROAROMATIC COMPOUNDS
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The reaction of indole (methylindoles) with a number of pyridine bases, imidazole, and benzimidazole in the presence of benzimidazolyl chlorides gave N-imidoyl derivatives of dihydro-α(γ)-3-indolylheterocyclic compounds, the aromatization of which under the influence of triphenylmethyl perchlorate or 1-oxo-2,2,6,6-tetramethylpiperidinium perchlorate leads to perchlorates of N-imidoyl heteroaromatic cations.
- Sheinkman, A. K.,Kozak, I. Yu.,Zemskii, B. P.
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p. 768 - 772
(2007/10/02)
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- N2-(ARYLSULFONYL)ARYLAMIDINES. SYNTHESIS AND PROPERTIES OF N2-(ARYLSULFONYL)ARYLAMIDINES AND THEIR N1-ACYL DERIVATIVES
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The reaction of carboxylic acid chlorides with N2-(arylsulfonyl)benzamidines was investigated.Conditions were found for the production of N2-arylsulfonyl-N1-acylbenzamidines and N2-arylsulfonyl-N1,N1-diacylbenzamidines.The hydrolysis and ammonolysis of the compounds were studied, and their IR spectra are discussed.It was established that the reactin of arenesulfonamides with the nitriles of aromatic acids in the presence of the alkaline or acidic catalysts leads to the formation of N2-(arylsulfonyl)amidines.
- Dubina, V. L.,Shebitchenko, L. N.,Pedan, V. P.,Yukhno, A. G.,Skripets, V. I.
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p. 691 - 696
(2007/10/02)
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