- Sulfur ylides generated from the reaction of adamantylidene and phenylcarbene with sulfur substrates
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Reaction of adamantylidene and phenylcarbene with ethylthiol, ethylene dithiol, allylethylsulfide, allylphenylsulfide, and trimethylenesulfide involves the formation of a sulfur ylide intermediate, followed by H-migration, 2,3-sigmatropic shift, or ring opening to give sulfides. The sulfur ylide formed in the reaction of phenylcarbene with trimethylenesulfide is directly observed by laser flash photolytic techniques.
- Romashin, Yuri N.,Liu, Michael T. H.,Hill, Brian T.,Platz, Matthew S.
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Read Online
- Yb(iii)-catalysedsyn-thioallylation of ynamides
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Reported herein is asyn-thioallylation of ynamides incorporating a sulfide moiety at the α-position and an allyl group at the β-position of the ynamide. The transformation is successful under ytterbium(iii)-catalysis, providing access to highly substituted thioamino-skipped-dienes with broad substrate scope. Thus, tetrasubstituted olefins (with four different functional groups: amide, phenyl, thioaryl/alkyl, and allyl on the carbon centers) are made in a single step from readily accessible ynamides, preserving complete atom economy. The reaction can be extended to the synthesis of selenoamino dienes by ynamidesyn-selenoallylation. DFT studies and control experiments provide insight into the reaction mechanism.
- Dutta, Shubham,Gandon, Vincent,Gogoi, Manash Protim,Mallick, Rajendra K.,Prabagar, B.,Sahoo, Akhila K.,Vanjari, Rajeshwer,Yang, Shengwen
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supporting information
p. 7521 - 7524
(2021/08/05)
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- A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent
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A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.
- Anselmi, Silvia,Liu, Siyu,Kim, Seong-Heun,Barry, Sarah M.,Moody, Thomas S.,Castagnolo, Daniele
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supporting information
p. 156 - 161
(2021/01/14)
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- Chemoselective rearrangement reactions of sulfur ylide derived from diazoquinones and allyl/propargyl sulfides
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Here, we describe three types of rearrangement reactions of sulfur ylide derived from diazoquinones and allyl/ propargyl sulfides. With Rh2(esp)2 as the catalyst, diazoquinones react with allyl/propargyl sulfides to form a sulfur ylide, which undergoes a chemoselective tautomerization/[2,3]-sigmatropic rearrangement reaction, a Doyle?Kirmse rearrangement/Cope rearrangement cascade reaction, or a Doyle?Kirmse rearrangement/elimination reaction, depending on the substituent of the sulfides. The protocol provides alkenyl and allenyl sulfides and multisubstituted phenols with moderate and high yields.
- Zhou, Cong-Ying,Yan, Sijia,Rao, Junxin
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supporting information
p. 9091 - 9096
(2020/12/02)
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- Ruthenium-catalyzed decarboxylative C-S cross-coupling of carbonothioate: synthesis of allyl(aryl)sulfide
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A novel ruthenium-catalyzed decarboxylative cross-coupling of carbonothioate is disclosed. This method provides straightforward access to the corresponding allyl(aryl)sulfide derivatives in generally good to excellent yields under mild conditions and feat
- Zheng, Ren-Hua,Guo, Hai-Chang,Chen, Ting-Ting,Huang, Qing,Huang, Guo-Bo,Jiang, Hua-Jiang
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p. 25123 - 25126
(2018/07/29)
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- Aqueous hemin catalyzed sulfonium ylide formation and subsequent [2,3]-sigmatropic rearrangements
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A mild hemin catalytic system for sulfonium ylide generation via a metal carbenoid and a subsequent [2,3]-sigmatropic rearrangement reaction in aqueous solvent is well-established, with the assistance of cyclodextrin (CD) and Triton X-100. The protocol displays high catalytic activity with a broad substrate scope of aryl/alkyl allyl sulfides and diazo reagents, affording homoallyl sulfide products in up to 99% yield. Notably, this catalytic system is successful for water-insoluble allyl sulfides but ineffective for allyl amines or allyl ethers. Moreover, an unprecedented cascade reaction of sulfonium ylide formation, [2,3]-sigmatropic rearrangement and C-H insertion was reported.
- Xu, Xiaofei,Li, Chang,Tao, Zhihao,Pan, Yuanjiang
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supporting information
p. 1245 - 1249
(2017/08/15)
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- Efficient reduction of sulfoxides with NaHSO3 catalyzed by I2
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An efficient method for the deoxygenation of sulfoxides into their corresponding sulfides at room temperature using NaHSO3 in the presence of catalytic I2 has been reported.
- Abbasi, Mohammad,Mohammadizadeh, Mohammad Reza,Moradi, Zahra
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p. 6610 - 6613
(2015/11/09)
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- Method of manufacturing compds. Allylnaphthol
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PROBLEM TO BE SOLVED: To provide a production method of an allyl compound of carrying out the dehydration allylation of a substrate having S, C or N which is a nucleophilic atom, especially S under the presence of a catalyst system consisting of a catalyst precursor having a specific structure and a specific ligand. SOLUTION: The production method of allyl compounds comprises as follow. A catalyst precursor chosen from Formula (1) and Formula (2) and a ligand are mixed, or a catalyst precursor, an allyl alcohol, and a ligand are mixed, then allyl alcohols and a substrate are blended and made to react. The ligand is quinaldic acid or picolinic acid, and the substrate is thiols, thiocarboxylic acids or the like. [Ru(C5H5)(CH3CN)3]PF6(1). [Ru[C5(CH3)5](CH3CN)3]PF6(2). COPYRIGHT: (C)2012,JPOandINPIT
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Paragraph 0026-0033; 0062
(2018/06/26)
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- Rh(II)-Catalyzed [2,3]-Sigmatropic Rearrangement of Sulfur Ylides Derived from Cyclopropenes and Sulfides
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(Chemical Equation Presented) A new type of Rh2(OAc)4-catalyzed [2,3]-sigmatropic rearrangement of sulfur ylides is reported. A series of cyclopropenes were successfully employed for [2,3]-sigmatropic rearrangement by a reaction with either allylic or propargylic sulfides. Under the optimized conditions, the reaction afforded the products in moderate to excellent yields. In these transformations, the vinyl metal carbenes generated in situ from the cyclopropenes were effectively trapped by sulfides, resulting in the formation of corresponding products upon [2,3]-sigmatropic rearrangements.
- Zhang, Hang,Wang, Bo,Yi, Heng,Zhang, Yan,Wang, Jianbo
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supporting information
p. 3322 - 3325
(2015/07/15)
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- Expanding the horizon of intermolecular trapping of in situ generated α-oxo gold carbenes: Efficient oxidative union of allylic sulfides and terminal alkynes via C-C bond formation
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With a new P,S-bidentate phosphine as the ligand to gold(i), the α-oxo gold carbenes generated in situ via gold-catalyzed intermolecular oxidation of terminal alkynes were effectively trapped by various allylic sulfides, resulting in the formation of α-aryl(alkyl)thio-γ,δ- unsaturated ketones upon facile [2,3]sigmatropic rearrangements. This journal is the Partner Organisations 2014.
- Li, Jiabin,Ji, Kegong,Zheng, Renhua,Nelson, Jonathan,Zhang, Liming
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supporting information
p. 4130 - 4133
(2014/04/03)
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- Catalyst-free imidation of allyl sulfides with chloramine-T and subsequent [2,3]-sigmatropic rearrangement
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A facile synthesis of various allyl sulfonamides based on imidation of allyl sulfides with chloramine-T and subsequent [2,3]-sigmatropic rearrangement has been achieved without metal catalysts. The reaction completes smoothly within 10 min, providing excellent yields in environment friendly solvent of alcohol. Functional groups such as bromine, hydroxyl, protected amido and aldehyde are tolerant under this condition.
- Jiang, Yubo,Mo, Fanyang,Qiu, Di,Kuang, Chunxiang,Zhang, Yan,Wang, Jianbo
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p. 2029 - 2035
(2012/11/07)
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- Reactions of 2-(α-Haloalkyl)thiiranes with nucleophilic reagents: V.* Reactions of 2-(α-chloroalkyl)thiiranes with organolithium compounds
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2-(α-Haloalkyl)thiiranes reacted with methyl-, butyl-, and phenyllithium to give the corresponding allyl sulfides. The reactions of diastereoisomeric erythro-and threo-2-(1-chloroethyl)thiiranes with phenyllithium were stereospecific, and they afforded (E)-and (Z)-1-phenylsulfanylbut-2-enes, respectively. 3-Chloromethyl-2,2- dimethylthiirane and phenyllithium gave rise to a mixture of 3-methyl-3-phenylsulfanylbut-1-ene and 3-methyl-1-phenylsulfanylbut-2-ene. The reactions of 2-chloromethylthiiranes with phenyllithium and methyllithium in the presence of a catalytic amount of copper(I) iodide (10 mol %) led to the formation of substituted thiiranes as the major products. Mechanisms of the observed transformations are discussed. Pleiades Publishing, Ltd., 2010.
- Tomashevskii,Sokolov,Potekhin
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experimental part
p. 1822 - 1825
(2011/04/17)
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- Highly efficient catalytic dehydrative S-allylation of thiols and thioic S-acids
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A SH-selective allylation method using [CpRu(2-quinolinecarboxylato) (η3-C3H5)]PF6 has been realized in various solvents including aqueous media to give allyl sulfides and allyl S-thioates, demonstrating the potential applicability to lipopeptide chemistry.
- Tanaka, Shinji,Pradhan, Prasun Kanti,Maegawa, Yusuke,Kitamura, Masato
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supporting information; experimental part
p. 3996 - 3998
(2010/07/06)
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- Fast ruthenium-catalysed allylation of thiols by using allyl alcohols as substrates
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The allylation of aromatic and aliphatic thiols, by using allyl alcohols as substrates, requires only minutes at ambient temperature with either a Ru Iv catalyst, [Ru(Cp*)(n3CH5)(CH 3CN)2](PF6)2 (2; Cp* = pentamethylcyclopentadienyl) or a combination of [Ru(Cp*)(CH 3CN)3](PF6) and camphor sulfonic acid. Quantitative conversion is normal and the catalyst possesses high functional-group tolerance. The use of [Ru(Cp*)(CH3CN) 3](PF6) alone affords poor results. A comparison is made to the results from catalytic runs based on the use of carbonates rather than alcohols, by using 2 as the catalyst, and it is shown that the products from the alcohols are formed faster, so there is no advantage in using a carbonate substrate. The observed branched-to-linear (b/1) ratios when using substituted alcohols decrease with time suggesting that the catalysts isomerise the products. A new methodology from which one can select the desired isomeric product is proposed. DFT calculations and NMR spectroscopic measurements, by using an arene sulfonic acid as co-catalyst, suggest that 6-complexes are not relevant for the catalytic system. Moreover, the DFT results indicate that l)any rf-complexes from the acids RC6H4SO 3H result from deprotonation of the acid, 2) complexation of the thiol, via the deprotonated sulfur atom, is preferred over complexation of the O atom of the sulfonate, RC6H4SO3and 3) a sulfonate O-atom complex will be difficult to detect.
- Zaitsev, Alexey B.,Caldwell, Helen F.,Pregosin, Paul S.,Veiros, Luis F.
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scheme or table
p. 6468 - 6477
(2010/02/28)
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- Allyl sulfides are privileged substrates in aqueous cross-metathesis: Application to site-selective protein modification
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Allyl sulfides undergo efficient cross-metathesis in aqueous media with Hoveyda-Grubbs second generation catalyst 1. The high reactivity of allyl sulfides in cross-metathesis was exploited in the first examples of cross-metathesis on a protein surface. S-Allylcysteine was incorporated chemically into the protein, providing the requisite allyl sulfide handle. Preliminary efforts to genetically incorporate S-allylcysteine into proteins are also reported. Copyright
- Lin, Yuya A.,Chalker, Justin M.,Floyd, Nicola,Bernardes, Goncalo J. L.,Davis, Benjamin G.
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supporting information; experimental part
p. 9642 - 9643
(2009/02/04)
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- Indium-mediated allylation of heteroaryl, benzyl, and cinnamyl thiocyanates: A novel route for 3-(allylsulfanyl)-1H-indoles
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Heteroaryl, benzyl, and cinnamyl thiocyanates undergo smooth allylation with allyl bromide in the presence of indium or zinc metal in THF at room temperature to produce the corresponding allyl sulfides in good yields and with high selectivity. Copyright
- Yadav,Subba Reddy,Chandrakanth,Hara Gopal
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supporting information; experimental part
p. 1082 - 1083
(2009/12/03)
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- The epoxy-Ramberg-Baecklund reaction (ERBR): A sulfone-based method for the synthesis of allylic alcohols
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The epoxy-Ramberg-Baecklund reaction (ERBR) is outlined, in which α,β-epoxy sulfones are converted into a range of mono-, di- and tri-substituted allylic alcohols, on treatment with base. Modification of this method enabled the preparation of enantio-enriched allylic alcohols following the diastereoselective epoxidation of enantio-enriched vinyl sulfones that were accessed efficiently from the chiral pool. The scope, optimisation and limitations of the ERBR as a method for the preparation of allylic alcohols are discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Evans, Paul,Johnson, Paul,Taylor, Richard J. K.
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p. 1740 - 1754
(2007/10/03)
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- A mild and highly convenient chemoselective alkylation of thiols using Cs2CO3-TBAI
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A mild and improved method for the synthesis of thioethers has been developed. In the presence of cesium carbonate, tetrabutylammonium iodide, and DMF, various alkyl and aryl thiols underwent S-alkylation to afford structurally diverse sulfides in high yield. Unprotected mercaptoalcohols and thioamines reacted chemoselectively at the sulfur moiety exclusively. An example of a one-pot, solid-phase synthesis of a thioether is also described.
- Salvatore, Ralph Nicholas,Smith, Robert A.,Nischwitz, Adam K.,Gavin, Terrence
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p. 8931 - 8935
(2007/10/03)
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- CsF-Celite, an efficient solid state reagent for the syntheses of thioesters and thioethers
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Coupling reactions of a number of aliphatic, aromatic, and heterocyclic compounds bearing an acidic hydrogen atom attached to sulfur, with alkyl, acyl, benzyl, or benzoyl halides in acetonitrile with cesium fluoride-Celite are described. This procedure is convenient, efficient, and practical for the preparation of thioethers and thioesters. Springer-Verlag 2005.
- Shah, Syed T. A.,Khan, Khalid M.,Hussain, Hidayat,Hayat, Safdar,Voelter, Wolfgang
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p. 1583 - 1589
(2007/10/03)
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- Synthesis of allylic sulfides via cleavage of S-S bonds promoted by zinc metal in DMF
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Cleavage of S-S bonds was achieved without any activation or catalysis, with a Zn/DMF system and subsequent treatment with allylic bromide afforded allylic sulfides in good to excellent yields.
- Du, Jingxing,Zheng, Renwei,Li, Xinsheng
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p. 180 - 181
(2007/10/03)
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- One-pot synthetic method of allyl sulfides: Samarium-induced allyl bromide mediated reduction of alkyl thiocyanates and diaryl disulfides in methanolic medium
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A convenient synthetic method of allyl sulfides by the treatment of alkyl thiocyanates or diaryl disulfides with Sm and allyl bromide in methanol has been developed.
- Zhan, Zhuang-Ping,Lang, Kai
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p. 1370 - 1371
(2007/10/03)
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- Diselenides and Allyl Selenides as Glutathione Peroxidase Mimetics. Remarkable Activity of Cyclic Seleninates Produced in Situ by the Oxidation of Allyl ω-Hydroxyalkyl Selenides
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A series of aliphatic diselenides and selenides containing coordinating substituents was tested for glutathione peroxidase (GPx)-like catalytic activity in a model system in which the reduction of tert-butyl hydroperoxide with benzyl thiol to afford dibenzyl disulfide and tert-butyl alcohol was performed under standard conditions and monitored by HPLC. Although the diselenides showed generally poor catalytic activity, allyl selenides proved more effective. In particular, allyl 3-hydroxypropyl selenide (25) rapidly generated 1,2-oxaselenolane Se-oxide (31) in situ by a series of oxidation and [2,3]sigmatropic rearrangement steps. The remarkably active cyclic seleninate 31 proved to be the true catalyst, reacting with the thiol via a postulated mechanism in which the thioseleninate 32 is first produced, followed by further thiolysis to selenenic acid 33 and oxidation-dehydration to regenerate 31. In contrast to catalysis with GPx, formation of the corresponding selenenyl sulfide 34 comprises a competing deactivation pathway in the catalytic cycle of 31, as a separate experiment revealed that authentic 34 was a much less effective catalyst than 31. 1,2-Oxaselenane Se-oxide (37), the six-membered homologue of 31, was formed similarly from allyl 4-hydroxybutyl selenide (26), but proved a less effective catalyst than 31. Compounds 31 and 37 are the first examples of unsubstituted monocyclic seleninate esters.
- Back, Thomas G.,Moussa, Ziad
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p. 13455 - 13460
(2007/10/03)
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- A novel method for the synthesis of allylic sulfides from disulfides and allylytterbium bromide
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In presence of trace of methyl iodide (Mel), allylytterbium bromide is formed by the reaction of metallic ytterbium and allylic bromide, which reacts with disulfides to give the corresponding allylic sulfides in good yields under mild and neutral conditions.
- Su,Li,Zhang,Li
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p. 263 - 264
(2007/10/03)
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- Synthesis and properties of β- and γ-aminoalkyl sulfides
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Reactions of mercaptans with allyl chloride, hydrobromination of the resulting allyl alkyl sulfides, and condensation of β-bromoalkyl sulfides with secondary amines were studied. The resulting β- and γ-aminoalkyl sulfides wre tested in gas treatment to re
- Krivonogov,Murinov,Miftakhov,Spirikhin
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p. 269 - 277
(2007/10/03)
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- A novel synthesis of allyl sulfides and allyl selenides via Sm-BiCl3 system in aqueous media
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Allyl sulfides and allyl selenides are synthesized via the reaction of allyl bromide with disulfides and diselenides promoted by the Sm-BiCl3 system in aqueous media in moderate to good yields.
- Zhan, Zhuangping,Lu, Genliang,Zhang, Yongmin
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p. 280 - 281
(2007/10/03)
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- Preparation of thioethers using SN1-active halides and zinc mercaptides
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SN1-Active (tertiary alkyl, allylic and benzylic) halides react with zinc mercaptides, prepared in situ by contacting mercaptans with either zinc carbonate or zinc sulphide, under optimised conditions, to afford thioethers in moderate to very good yields (50-95 percent). The method is particularly useful for the preparation of thioethers with at least one bulky alkyl group.
- Srinivas, S.,Srinivas, P.,Gurudutt, K. N.
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p. 1174 - 1176
(2007/10/03)
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- A novel synthesis of allyl sulfides in aqueous media promoted by indium
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Allyl bromides react smoothly with sodium alkyl thiosulfates promoted by indium in aqueous media to give allyl sulfides in moderate to good yields.
- Zhan, Zhuangping,Zhang, Yongmin
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p. 493 - 497
(2007/10/03)
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- A Novel Synthesis of Allyl Sulfides by Organosamarium Reagents
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Organosamarium reagents react with sodium alkyl thiosulfates to afford allyl Sulfides; a reaction mechanism involving organosamarium(II) and Organosamarium (III) intermediates is suggested.
- Zhan, Zhuangping,Zhang, Yongmin
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p. 148 - 149
(2007/10/03)
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- The synthesis of allyl sulfides by organosamarium reagent
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Organosamarium reagent reacts with disulfides to afford allyl sulfides in THF.
- Yu, Mingxin,Zhang, Yongmin
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p. 2743 - 2748
(2007/10/03)
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- THIOLS, UNSYMMETRICAL SULFIDES AND THIOACETALS FROM THE NEW REAGENT: TRIISOPROPYLSILANETHIOL
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Triisopropylsilanethiol (HSTIPS, 1), easily prepared in 98percent yield from H2S and TIPSCl, is efficiently alkylated in a selective manner with 10 and 20 alkyl halides or tosylates through its potassium thiolate (2c) to provide RSTIPS (3) in excellent yields.Compound 3 provides a convenient source of alkanethiols (4), unsymmetrical dialkyl sulfides (5) and thioacetals (6).
- Miranda, Edgar I.,Diaz, Michael J.,Rosado, Izander,Soderquist, John A.
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p. 3221 - 3224
(2007/10/02)
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- The allyloxycarbonylaminomethyl group: A new allytic protection for the thiol group of cysteine
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S-Allocam derivatives of thiols in general and cysteine in particular are selectively and readily deprotected through palladium catalyzed hydrostannolysis. They are perfectly stable in the basic conditions of Fmoc-removal, but only marginally stable in the acidic conditions of t-Bu, Boc removal.
- Kimbonguila, Andre Malanda,Merzouk, Ahmed,Guibe, Francois,Loffet, Albert
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p. 9035 - 9038
(2007/10/02)
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- Naphthalene-Catalysed Lithiation of Allylic and Benzylic Mesylates: A New Method for Allyl, Methallyl, and Benzyl Lithium
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The reaction of allylic or benzylic mesylates (1) with an excess of lithium powder and a catalytic amount of naphthalene (4 mol percent) in THF at -78 deg C leads to a solution of the corresponding organolithium derivatives, which by treatment with different electrophiles yield the expected products 2-7.As an alternative route, the process can be carried out at 0 deg C by adding the corresponding mesylate together with the electrophile to a suspension of the activated lithium in THF, in a Barbier-type reaction.
- Guijarro, D.,Mancheno, B.,Yus, M.
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p. 4593 - 4600
(2007/10/02)
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- A Facile Synthesis of Unsymmetrical Sulfides under Phase Transfer Conditions
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An efficient synthesis of unsymmetrical sulfides (3) is described by reacting S-alkylisothiouronium salts (1) with alkyl halides (2) under liquid-liquid phase transfer catalyst conditions.
- Hengchang, Chen,Zhenzhong, Liu,Wei, Liu
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p. 3313 - 3316
(2007/10/02)
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- An Efficient Synthesis of Unsymmetrical Sulfides Using Liquid-Liquid Phase-Transfer Catalysis
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The reaction between alkyl ethaneimidothioate hydrohalides (1-alkylthioethaniminium halides) and organic halides gives unsymmetrical sulfides in good yields under liquid-liquid phase-transfer conditions.
- Takido, Toshio,Itabashi, Kunio
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p. 817 - 819
(2007/10/02)
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- A Facile Synthesis of Functionalised Organic Sulphides
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Thioiminium salts and organic halides or Michael acceptors, in the absence of solvent and at ambient temperature, give title compounds in excellent yields.
- Singh, Harjit,Batra, Manohar S.
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p. 1111 - 1112
(2007/10/02)
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- Palladium-Catalyzed Synthesis of Allylic and Benzylic Sulifides from the Corresponding Dithiocarbonates
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Allylic and benzylic sulfides are prepared from O-(2-alkenyl) or S-(2-alkenyl) S-alkyl and O-benzyl S-alkyl dithiocarbonates in the presence of palladium(0)-phosphine complex as a catalyst.
- Lu, Xiyan,Ni, Zhijie
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- Free-Radical Chain Substitution Reactions (SH2') of Alkenyl-, Alkynyl-, and (Alkenyloxy)stannanes
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Free-radical chain substitution reactions of allyltributylstannane were observed with PhSSPh, PhCH2SSCH2Ph, PhSeSePh, PhSO2Cl, n-PrSO2Cl, or CCl3SO2Cl, where the attacking radicals leading to allylic rearrangement with displacement of Bu3Sn(radical) were PhS(radical), PhCH2S(radical), PhSe(radical), PhSO2(radical), n-PrSO2(radical), and CCl3(radical), respectively.Allylic rearrangement was also observed in the SH2' reaction of crotyltributylstannane with PhSSPh, PhCH2SSCH2Ph, PhSO2Cl, or n-PrSO2Cl.Propargyltriphenylstannane underwent SH2' substitution to form the allenic substitution products with PhSO2Cl, n-PrSO2Cl, CCl4, and CHCl3 while 2-butynyltriphenylstannane formed the 1,2-butadiene with PhSO2Cl or n-PrSO2Cl.Reaction of (1-cyclohexenyloxy)tributylstannane with CCl4 or BrCCl3 formed α-(trichloromethyl)cyclohexanone.With HCBr3 the initially formed α-(dibromomethyl)cyclohexanone readily underwent dehydrobromination to form α-(bromomethylene)cyclohexanone. tributylstannane formed α-(trichloromethyl)isobutyraldehyde with CCl4 or BrCCl3.Reaction with HCBr3 gave a mixture of α-(dibromomethyl)isobutyraldehyde and 1-(dibromomethyl)-2,2-dimethyloxirane.
- Russell, Glen A.,Herold, Lourdes Lucas
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p. 1037 - 1040
(2007/10/02)
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- A Facile One-pot Synthesis of Sulfides from Alkyl Halides and Alcohols Using Tetramethylthiourea
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Sulfides can be readily prepared under mild conditions by a reaction of tetramethylthiourea with alkyl halides and alcohols in the presence of sodium hydride in satisfactory yields.The scope and limitation of this method are also presented.
- Fujisaki, Shizuo,Fujiwara, Isamu,Norisue, Yasumasa,Kajigaeshi, Shoji
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p. 2429 - 2430
(2007/10/02)
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- Synthesis of Unsymmetrical Functionalised Organic Sulphides
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Acyclic thioiminium salts and the condensed thiazolium salts in the presence of aqueous sodium hydroxide as such or under base catalyzed phase transfer catalysis conditions react with appropiate organic halides to provide corresponding unsymmetrical functionalized organic sulphides.With aqueous sodium hydroxide, thioiminium salts provide the disulphides corresponding to incipient thiol.
- Singh, Harjit,Batra, Manohar S.,Singh, Paramjit
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p. 131 - 136
(2007/10/02)
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- Nucleophilic Substitution of Alkyl Halides by Zinc Salts: Part 4-Synthesis of Thioethers and Thiolesters
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A variety of alkyl halides including tertiary alkyl halides react smoothly with the zinc salts of thiols and thiolcarboxylic acids yielding thioethers and thiolesters.
- Rajanikanth, B.,Ravindranath, B.
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p. 1043 - 1045
(2007/10/02)
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- Synthesis of Unsymmetrical Thioethers Using Solid-Liquid Phase-transfer Catalysis
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The title compounds have been synthesised from appropriate organic halides and thioimminium salts (1) in moderate to good yields under solid-liquid phase-transfer catalysis using Triethylbenzylammonium chloride (TEBA) as a catalyst, solid KOH as a base in chloroform.
- Singh, Paramjit,Batra, Manohar S.,Singh, Harjit
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- Synthesis of Functionalised, Unsymmetrical Organic Sulphides - Thioacetamide as a Sulphur Transfer Reagent
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In a novel approach, unsymmetrical organic sulphides (IIa-h) have been obtained from appropriate organic halides and sulphonium salts (I) - a source of incipient thiolate ions.
- Singh, Harjit,Malhotra, Nageshwar,Batra, Manohar S.
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p. 272 - 273
(2007/10/02)
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- Gas Phase Reactions, 24. The Thermal Generation of Thiocarbonyl Compounds
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Thiocarbonyl derivatives R1R2C=S with R1, R2 = H, CH3, C6H5 can be generated thermally in the gas phase from a variety of precursors.Especially advantageous are the cleavage of propene from allyl sulfides or, for their preparation in pure form, the pyrolysis of dithietane or trithiolane derivatives.Photoelectron spectroscopy proves to be well-suited for gas analysis in the flow tube used, for the optimization of the decomposition conditions, and via assignment of the observed ionization patterns for the characterization of the thioaldehydes and thioketones prepared.
- Bock, Hans,Hirabayashi, Takakuni,Mohmand, Shamsher
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p. 492 - 503
(2007/10/02)
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- GAS-PHASE THERMOLYSIS OF SULFUR COMPOUNDS. PART V. METHYL ALLYL, DIALLYL AND BENZYL ALLYL SULFIDES
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The title compounds have been pyrolyzed in a stirred-flow system, at temperatures within the range 315-418 deg C and pressures between 2 and 15 torr.Under these conditions, the products observed were propene and the polymers of thiomethanal, allyl thioaldehyde and benzyl thioaldehyde.Diallyl sulfide was further in a static system, over the temperature range of 227-256 deg C and initial pressures between 90 and 255 torr.The reactions showed first-order kinetics and the rate coefficients yielded the following Arrhenius equations: methyl allyl sulfide: k (sec-1) = 1E11.23+-0.25 exp(-160+-3 kJ/mol.RT); diallyl sulfide: k (sec-1) = 1E11 .01+-0.06 exp(-138.2+-0.7 kJ/mol.RT); benzyl allyl sulfide: k (sec-1) 1E10.93+-0.18 exp(-141+-2 kJ/mol.RT).The Arrhenius parameters are consistent with a unimolecular mechanism involving six-centered cyclic transition states yielding propene and thioaldehyde.The results are discussed in relation to ally ethers and amines reported in the literature
- Martin, Gonzalo,Ropero, Marcos,Avila, Ramona
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p. 213 - 220
(2007/10/02)
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- Preparation of organic sulfone compounds
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An in-situ process for preparing organic sulfone compounds by oxidizing the corresponding sulfide compound with a mixture of hydrogen peroxide, a carboxylic acid in the presence of a catalytic amount of a mineral acid or an organic sulfonic acid.
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