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Thionyl Chloride (thionyl + chloride)
Selected AbstractsChemInform Abstract: Iodine-Catalyzed Efficient Synthesis of Symmetrical Diaryl Sulfoxides from Arenes and Thionyl Chloride under Solvent-Free Conditions.CHEMINFORM, Issue 18 2008Hong She Wang Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source] Atypical Oxidation Reaction by Thionyl Chloride: Easy Two-Step Synthesis of N-Alkyl-1,4-dithiines.CHEMINFORM, Issue 17 2007Alain Valla Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source] Conversion of Epoxides to ,-Chlorohydrins with Thionyl Chloride and ,-Cyclodextrin in Water.CHEMINFORM, Issue 52 2005K. Surendra Abstract For Abstract see ChemInform Abstract in Full Text. [source] Condensed Thiophenes and Selenophenes: Thionyl Chloride and Selenium Oxychloride as Sulfur and Selenium Transfer Reagents.CHEMINFORM, Issue 38 2002Ramiya R. Amaresh Abstract For Abstract see ChemInform Abstract in Full Text. [source] Novel Synthetic Strategy towards the Efficient Synthesis of Substituted Bis(pyrazolyl)(2-pyridyl)methane Ligands,EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 21 2010Alexander Hoffmann Abstract A general one-pot synthesis of new substituted heteroscorpionate ligands is presented. These mixed-functionality ligands were obtained in a catalyzed Peterson rearrangement starting from the substituted pyrazole, thionyl chloride, and an aldehyde. Thus, the synthesis of polyfunctional tridentate ligands is enabled, and they contain, besides the two pyrazole groups, other functionalities relevant for coordination chemistry. Additionally, the steric hindrance is easily defined in the ligands by the substitution of the pyrazole rings. By combination of the versatility in donor function and steric demand, a systematic tuning of the properties of the bis(pyrazolyl)methane ligands is possible. The synthesis and full characterization of 11 bis(pyrazolyl)methane ligands are reported. Two of these were structurally characterized as well. [source] Ring Expansion of 2-(,-Hydroxyalkyl)azetidines: A Synthetic Route to Functionalized PyrrolidinesEUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 19 2008François Durrat Abstract A series of 2-(,-hydroxyalkyl)azetidines synthesized from enantiomerically pure ,-amino alcohols and presenting various patterns both on the four-membered ring and on the adjacent hydroxy group were treated with either thionyl chloride or methanesulfonyl chloride in the presence of triethylamine. The thus-prepared 2-(,-chloro- or ,-methanesulfonyloxyalkyl)azetidines were shown to rearrange stereospecifically into 3-(chloro- or methanesulfonyloxy)pyrrolidines. When this rearrangement is conducted in the presence of an added nucleophile (NaN3, KCN, KOH, or NaOAc), the produced pyrrolidine incorporates the added nucleophile at C-3 stereospecifically. The relative configuration of the substituents in the formed pyrrolidines is consistent with a mechanism involving the formation of an intermediate bicyclic aziridinium ion, which is opened regioselectively at the bridgehead carbon atom. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) [source] Synthesis and Conformational Analysis of Tetrahydroisoquinoline-Fused 1,3,2-Oxazaphospholidines and 1,2,3-OxathiazolidinesEUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 8 2008Ildikó Schuster Abstract The cyclizations of tetrahydroisoquinoline 1,2-amino alcohols with phenylphosphonic dichloride, bis(2-chloroethyl)phosphoramidic dichloride, thionyl chloride and sulfuryl chloride were utilized to synthesize 1,5,6,10b-tetrahydro-1,3,2-oxazaphospholo[4,3- a]isoquinolines (2, 3), 1,5,10,10a-tetrahydro-1,3,2-oxazaphospholo[3,4- b]isoquinolines (8, 9), 1,5,6,10b-tetrahydro-1,2,3-oxathiazolo[4,3- a]isoquinolines (4,6) anda 1,5,10,10a-tetrahydro-1,2,3-oxathiazolo[3,4- b]isoquinoline (11), which are the first representatives of these ring systems. NMR spectroscopic analysis revealed the existence of conformational equilibria that are fast on the NMR timescale. Theoretical DFT calculations pointed to the participation of generally two preferred conformers in the conformational equilibria; the positions of the equilibria were indicated by the experimental NMR spectroscopic parameters, and they are in good agreement with the theoretically calculated energy differences of the participating conformers. For two compounds, which could be not isolated (10, 12), both the preferred conformers and the stereochemistry could be concluded from the DFT calculation results. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) [source] Studies on organophosphorus compounds: Synthesis and reactions of [1,2,4,3]triaza-phospholo[4,5- a]quinoxaline derivativeHETEROATOM CHEMISTRY, Issue 5 2008Hassan M. Moustafa 2,4-Bis-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson's reagent) (1) reacted with 2-hydrazino-3-methyl-quinoxaline (2) to give [1,2,4,3]-triazaphospholo[4,5- a]quinoxaline derivative 3. The Mannich reaction using different amines on compound 3 gave Mannich bases 4a,d. Also, compound 3 reacted with formaldehyde to give the corresponding 2-hydroxymethyl derivative 5, which upon reaction with thionyl chloride gave the corresponding chloromethyl derivative 6. Treatment of compound 6 with some thiols yielded the corresponding sulfides 7a,d. Acylation of compound 3 gave acylated compounds 8a,b. Compound 9, which was prepared through the reaction of compound 3 with ethyl cyanoacetate, was investigated as a starting material for the synthesis of some new heterocyclic systems 10,13. Also, reaction of compound 9 with carbon disulfide and 2 equivalents of methyl iodide in a one-pot reaction yielded the corresponding ketene-S,S-acetal 14, which in turn reacted with bidentates to give some new heterocycles 15,17. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:520,529, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20473 [source] Structures and properties of two diastereomeric cyclic sulfites derived from cis -3,4-di- tert -butylthiolane-3,4-diol and thionyl chlorideHETEROATOM CHEMISTRY, Issue 7 2003Sanae Tanaka cis-3,4-Di-tert-butylthiolane-3,4-diol (1) was treated with an equimolar amount of thionyl chloride in the presence of triethylamine or pyridine in several solvents of different polarity to furnish two diastereomeric sulfites 2a and 2b generally in excellent combined yields. Although 2a was consistently formed as the major diastereomer when pyridine was used as the base, 2a and 2b were formed in approximately equal amounts when triethylamine was used as the base in polar solvents. X-ray crystallographic analyses revealed that the SO group of 2a is anti to the thiolane ring and that of 2b syn to the thiolane ring. Density functional theory calculations (B3LYP/6-31G* level) revealed that 2a is less stable than 2b by 1.28 kcal mol,1, although 2a was formed generally as the predominant diastereomer. Spectroscopic data of 2a and 2b are discussed with emphasis on comparison with those obtained by calculations. Treatment of 2a and 2b with m-chloroperbenzoic acid resulted in the oxidation of the divalent sulfur atom of the thiolane ring and not the sulfite sulfur atom. The above oxidations took place exclusively at the syn-side with respect to the tert-butyl groups.© 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:587,595, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10192 [source] Enantioselective Copper-Catalysed Allylic Alkylation of Cinnamyl Chlorides by Grignard Reagents using Chiral Phosphine-Phosphite LigandsADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 11-12 2010Wibke Lölsberg Abstract The copper(I)-catalysed SN2,-type allylic substitution of E -3-aryl-allyl chlorides (cinnamyl chlorides) using Grignard reagents represents a powerful method for the synthesis of compounds carrying a benzylic stereocentre. By screening a small library of modular chiral phosphine-phosphite ligands a new copper(I)-based catalyst system was identified which allows the performance of such reactions with exceptional high degrees of regio- and enantioselectivity. Best results were obtained using TADDOL-derived ligands (3,mol%), copper(I) bromide,dimethyl sulfide (CuBr,SMe2) (2.5,mol%) and methyl tert -butyl ether (MTBE) as a solvent. Various (1-alkyl-allyl)benzene derivatives were prepared with up to 99% ee (GC) in isolated yields of up to 99%. In most cases the product contained less than 3% of the linear regioisomer (except for ortho -substituted substrates). Both electron-rich and electron-deficient cinnamyl chlorides were successfully employed. The absolute configuration of the products was assigned by comparison of experimental and calculated CD spectra. The substrates were prepared from the corresponding alcohols by reaction with thionyl chloride. Initially formed mixtures of regioisomeric allylic chlorides were homogenised by treatment with CuBr,SMe2 (2.5,mol%) in the presence of triphenyl phosphine (PPh3) (3,mol%) in MTBE at low temperature to give the pure linear isomers. In reactions with methylmagnesium bromide (MeMgBr) an ortho -diphenylphosphanyl-arylphosphite ligand with an additional phenyl substituent in ortho, -position at the aryl backbone proved to be superior. In contrast, best results were obtained in the case of higher alkyl Grignard reagents (such as ethyl-, n -butyl-, isopropyl-, and 3-butenylmagnesium bromides) with a related ligand carrying an isopropyl substituent in ortho, -position. The method was tested on a multi-mmol scale and is suited for application in natural product synthesis. [source] Preparation and characterization of polymer/multiwall carbon nanotube/nanoparticle nanocomposites and preparation of their metal complexesJOURNAL OF APPLIED POLYMER SCIENCE, Issue 1 2010Ahmad Nozad Golikand Abstract Carbon nanotube-polymer nanocomposites were synthesized and characterized successfully. In this work, multiwall carbon nanotubes (MWCNT) were opened using HNO3/H2SO4 mixture and filled by metal nanoparticles such as silver nanoparticles through wet-chemistry method. The oxidized MWCNT were reacted subsequently with thionyl chloride, 1,6-diaminohexane, producing MWNT-amine functionalized. Then the MWCNT containing metal nanoparticles were used as a monomer with different weight percentages in melt polymerization with An and CNCl separately. Furthermore, the polyamide and polytriazine modified MWCNT were used for the preparation of metal ion complexes such as Fe+2 and La+3. The structures and properties of nanocomposites were evaluated by TEM, DSC, TGA, and FT-IR methods. The chelating behavior and sorption capacities of prepared nanocomposites were carried out by using some metal ions. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010 [source] Synthesis and characterization of dendronized aromatic polyamides with bromomethyl groups in the peripheryJOURNAL OF APPLIED POLYMER SCIENCE, Issue 1 2008Yanru Miao Abstract This paper focused on the synthesis of novel functionalized dendronized aromatic polyamides, which contained a polyamide backbone and polyamide dendrons decorated with bromomethyl groups, by the macromonomer route. The new activating procedure of the synthesis of dendrons and macromonomers using thionyl chloride as an activating agent eliminated the protection/deprotection procedure and reduced side reactions. The structures of the dendrons, macromonomers, and polyamides were confirmed by FTIR, 1H NMR, 13C NMR, and elemental analysis. The properties of the resulting dendronized polyamides, which were compared with that of the linear polyamide (LP), were studied using GPC, XRD, TGA, DSC, inherent viscosity measurement, and solubility experiment. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008 [source] Use of copper(II)/ethylene diamine-cotton complex for the adsorption of residual dyesJOURNAL OF APPLIED POLYMER SCIENCE, Issue 3 2007Mohamed Hassen V. Baouab Abstract The chemical modification of cotton is performed by successive reactions with thionyl chloride followed by ethylene diamine (ED) to prepare aminoalkyl amino cotton namely ED-cotton. Evidence of attaching ethylene diamine groups onto cotton is provided by nitrogen determination and thermogravimetry analysis. Because of complexation, the ethylene diamine-grafted groups immobilizes Cu(II) ions from buffered solution at pH 6. The formation of a 1/1 complex is assessed by the adsorption limit values. The binary system [Cu(II)/ED-cotton] is then tested for the adsorption of two acid dyes (Acid Blue 25 and Calmagite) as ligands in the metal-coordinating process. The adsorption of Cu(II) onto ED-cotton and of the dyes onto Cu(II)/ED-cotton is followed spectrometrically. The observed stoichiometries of the ternary-formed complex [Dye/Cu(II)/ED-cotton] are 1/1/1 with Acid Blue 25 and 0.75/1/1 with Calmagite at 20°C. The Langmuir and Freundlich isotherms constants for the adsorption of the tested dyes onto Cu(II)/ED-cotton are evaluated from the experimental data, but better agreement is obtained by using the composite isotherm of Jossens. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 103: 1389,1396, 2007 [source] Microwave-assisted synthesis of quinolone derivatives and related compoundsJOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 5 2010Suhas Pednekar The Gould-Jacob type of reaction for the synthesis of ethyl 5-ethyl-8-oxo-5,8-dihydro-[1,3]-dioxolo[4,5-g]quinoline-7-carboxylate 4 has been carried out conventionally by the condensation between N -ethyl-3,4-methylenedioxyaniline 1 and diethyl ethoxymethylenemalonate 2 gave the unsaturated ester 3 and thermal cyclization in refluxing diphenyl oxide gave quinolone ethyl ester 4 and the results obtained were compared with single step microwave irradiation under solvent free conditions for the synthesis of 4. The esters on basic hydrolysis formed free acid 5, which, upon treatment with thionyl chloride gave the acid chloride 6. Treatment of acid chloride with o -phenylenediamine, hydrazine hydrate, ammonia, urea, and thiourea gave the amides (7,11). CS2 treatment in presence of KOH on 8 gave 12. We prepared 7,12 derivatives by conventional as well as microwave irradiation. These compounds have been characterized on the basis of IR, 1H NMR, MS, and elemental analysis. All the compounds prepared herein were screened for their antibacterial activity. Compounds 4, 5 possess promising antibacterial activity and compound 8 showed significant antibacterial activity. J. Heterocyclic Chem., (2010). [source] Synthesis of new 3-(trifluoromethyl)-1H -indoles by reduction of trifluoromethyloxoindolesJOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 4 2008Moônica M. Bastos This work describes the synthesis of new 3-trifluoromethylindoles. Different isatins were trifluoromethylated using (trifluoromethyl) trimethylsilane (Me3SiCF3) as a nucleophilic agent giving new 3-hydroxy-3-(trifluoromethyl)indolin-2-one. Different "one-step" procedures to transform the latter compounds into the reduced indoles were attempted, but failed. For the synthesis of the new trifluoromethylindoles the corresponding 2-oxo-3-(trifluoromethyl)indoles were reduced using borane/THF complex to furnish 3-(trifluoromethyl)indolin-3-ol that additionally were dehydrated using thionyl chloride in pyridine to give excellent yields of the desired products. [source] Synthesis of new heterocycles containing more than one 1,2,3-thia or selenadiazole ringsJOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 4 2007Mousa Al-Smadi The diketones 2a-d with different alkyl chain length are used for the synthesis of di-1,2,3-thia or selenadiazole derivatives 4a-d and 5a-d. The diketones 2a-d where prepared by a unique method through the reaction between the corresponding dibromoalkanes 1a-d and ethyl acetoacetate, which are transformed into the corresponding semicarbazone derivatives 3a-d. The di-1,2,3-thia or selenadiazole derivatives 4a-d and 5a-d were prepared from the semicarbazones derivatives 3a-d on oxidative cyclization with thionyl chloride and selenium dioxide respectively in high yield. [source] Synthesis, X-ray crystal structure and biological activities of ,-phenoxyl-1,2,3-thiadiazoleacetamideJOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 5 2003Wei Guang Zhao The annelation of 1,2,3-thiadiazole rings was accomplished by the reaction of N -acylhydrazone 2a bearing an adjacent ,-methyl with thionyl chloride to give ,-chloro- N -methyl-1,2,3-thiadiazole-4-acetamide 4 and was demonstrated by the X-ray crystal structure of its derivative 5a. A novel series of ,-substituted phenoxy- N -methyl-1,2,3-thiadiazole-4-acetamide 5 were synthesized through the reaction of the compound 4 and phenols. The results of bioassays show that the title compounds exhibit good anti-HBV activities. The crystal of compound 5a, N -methyl-,-2-bromophenyl-1,2,3-thiadiazole-4-acetamide, has been prepared and determined by X-ray diffraction. [source] Perhydro-1,3-diazepine-2,4-diones by cyclization of 4-ureidobutyric acids with thionyl chloride: A reinvestigationJOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 1 2000Roland Heckendorn The structures of the previously reported aryl-perhydro-1,3-diazepine-2,4-diones are shown to be pyrro-lidinone carboxamide derivatives by nmr spectroscopy. [source] Study of the Reactions of Fluorine-Containing Amides with Aldehydes and the Structures of the BisamidesCHINESE JOURNAL OF CHEMISTRY, Issue 6 2009Jingwei ZHAO Abstract The reactions of trifluoro or bromodifluoro acetamides with aromatic aldehydes in the presence of thionyl chloride and trifluoromethylsulfonic acid were investigated. Compared with the procedure reported previously, the yields were improved greatly and the reaction conditions were much milder. Both intra- and intermolecular weak interactions were discussed in detail based on the X-ray diffraction analysis of 3aa and 3ab. [source] | ||||||||||