- Regioselective reactions of sulfur, selenium and tellurium chlorides with allyl trimethyl silane
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Electrophilic addition of SCl2, SeCl2 and SeCl 4 to 2 equivalents of allyl trimethyl silane proceeds regioselectively to give bis[2-chloro-3-(trimethylsilyl)propyl] sulfide, selenide and selenium dichloride, respectively. The reaction with TeCl 4 affords only diallyl tellurium dichloride. The structures of the compounds were confirmed by 1H, 13C, 77Se and 125Te NMR techniques.
- Martynov, Alexander V.,Makhaeva, Natalia A.,Larina, Lyudmila I.,Amosova, Svetlana V.
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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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- 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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- Diallyl Trisulfide Is a Fast H2S Donor, but Diallyl Disulfide Is a Slow One: The Reaction Pathways and Intermediates of Glutathione with Polysulfides
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Diallyl trisulfide (DATS) reacts rapidly with glutathione (GSH) to release H2S through thiol-disulfide exchange followed by allyl perthiol reduction by GSH. Yet diallyl disulfide (DADS) only releases a minute amount of H2S via a sluggish reaction with GSH through an α-carbon nucleophilic substitution pathway. The results clarify the misunderstanding of DADS as a rapid H2S donor, which is attributed to its DATS impurity.
- Liang, Dong,Wu, Haixia,Wong, Ming Wah,Huang, Dejian
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supporting information
p. 4196 - 4199
(2015/09/15)
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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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- NaI/silica sulfuric acid as an efficient reducing system for deoxygenation of sulfoxides in poly ethylene glycol (PEG-200)
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Deoxygenation of structurally diverse sulfoxides including dialkyl, diaryl, aryl alkyl and allyl sulfoxides to the corresponding sulfides were carried out using a NaI/silica sulfuric acid reducing system at room temperature in poly ethylene glycol (PEG-200) in excellent yields.
- Zarei, Morteza,Ameri, Mohammad Aghil,Jamaleddini, Azar
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p. 259 - 263
(2013/08/26)
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- Regioselective addition of sulfur dichloride and selenium tetrachloride to diallyldimethylsilane as the method of preparation of eight-membered heterocycles containing silicon and chalcogens
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The electrophilic additiob of sulfur dichloride and selenium tetrachloride to diallyldimethylsilane proceeds strictly according Markownikoff rule and results in the formation of previously unknown saturated silicon-containing heterocycles, 5,5-dimethyl-3,7-dichloro-1,5-thiasilacyclooctane and 5,5-dimethyl-1,1,3,7-tetrachloro-1,5-selena(IV)silacyclooctane. The structure of heterocycles obtained was confi rmed by 1H, 13C NMR spectra, in the case of selenium-containing heterocycle, by 77Se NMR spectrum, among them the 2D HMBC spectrum. Pleiades Publishing, Ltd., 2010.
- Martynov,Makhaeva,Larina,Amosova
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experimental part
p. 1675 - 1677
(2011/03/18)
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- TAPC-promoted oxidation of sulfides and deoxygenation of sulfoxides
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Figure presented. 1,3,5-Triazo-2,4,6-triphosphorine-2,2,4,4,6,6- tetrachloride (TAPC) was found to be an efficient promoter for the oxidation of sulfides and deoxygenation of sulfoxides. Excellent yields, short reaction time, easy and quick isolation of the products, solvent-free process, and excellent chemoselectivity are the main advantages of this procedure.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Sheikh Arabi, Mehdi
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supporting information; experimental part
p. 6208 - 6213
(2010/11/04)
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- GARLIC PROCESSING
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A method of producing polysulfides comprising the step of adding elemental sulphur to an allicin-containing plant extract. In preferred embodiments, the plant extract is mechanically treated members of the genus Allium, especially garlic. In further preferred aspects of the invention, the plant extract and sulphur mixture is heated, and the pH is controlled to allow manipulation of the polysulfide chain length. The addition of organic bases, containing nitrogen lone pairs, allows further control of polysulfide chain length.
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Page/Page column 5-6; 8
(2008/12/05)
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- Mild and efficient deoxygenation of sulfoxides to sulfides with triflic anhydride/potassium iodide reagent system
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It was found that the combination of triflic anhydride/potassium iodide was an effective promoter for the deoxygenation of sulfoxides and gave the corresponding sulfides in excellent yield in acetonitrile at room temperature. It is worth mentioning that this reagent system is chemoselective and tolerates various functional groups, such as alkene, ketone, ester, aldehyde, acid, and oxime. Georg Thieme Verlag Stuttgart.
- Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Karimi, Ahmad
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experimental part
p. 2543 - 2546
(2009/04/04)
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- PROCESS FOR PRODUCING DIALLYL DISULFIDE
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The invention provides a process for forming diallyl disulfide. The process comprises A) mixing together sulfur and at least one alkali metal sulfide in an initial aqueous medium in which at least about 90 volume percent of said aqueous medium is water, such that a disulfide source is formed in said initial aqueous medium thereby forming a disulfide source-conatining aqueous medium, and B) mixing together at least a portion of said disulfide source-containing aqueous medium and at lease one allyl halide selected from allyl cloride, allyl bromide, or a mixture of any two or all three of these, in the absence of any additional solvent other than water, at a temperature in the range of about 40?C to about 60?C, such that diallyl disulfide is formed.
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Page/Page column 12-16
(2010/10/20)
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- Deoxygenation of sulfoxides and reductive coupling of sulfonyl chlorides, sulfinates and thiosulfonates using Silphos [PCl3-n(SiO 2)n] as a heterogeneous phosphine reagent
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Deoxygenation of sulfoxides to thioethers and reductive coupling of sulfonyl chlorides, sodium sulfinates and thiosulfonates to their corresponding disulfides were carried out by a heterogeneous phosphine reagent, Silphos [PCl3-n(SiO2)n] and molecular I2 in dry refluxing MeCN in high yields. Georg Thieme Verlag Stuttgart.
- Iranpoor, Nasser,Firouzabadi, Habib,Jamalian, Arezu
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p. 1447 - 1449
(2007/10/03)
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- Reactions of 2-allylthiobenzimidazole, -oxazole, -thiazole, and the isomeric thiones with dichlorocarbene
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The reactions of 2-allylthiobenzimidazole, -oxazole, and -thiazole, and the thiones formed from them on heating, with dichlorocarbene have been investigated under phase transfer catalysis conditions.
- Ramazanova,Tarakanova,Vagabov,Litvinova,Anisimov
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p. 201 - 206
(2007/10/03)
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- Thermal Degradation of Allyl Isothiocyanate in Aqueous Solution
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Allyl isothiocyanate in an aqueous solution was heated and refluxed at 100 °C for 1 h. The reaction mixtures were then extracted with methylene chloride and analyzed using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The mixtures in aqueous phase were analyzed by high-performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry (LC-MS) equipped with an atmospheric-pressure chemical ionization (APCI) interface. The compounds identified in the methylene chloride extracts included diallyl sulfide, diallyl disulfide, diallyl trisulfide, diallyl tetrasulfide, allyl thiocyanate, 3H-1,2-dithiolene, 2-vinyl-4H-1,3-dithiin, 4H-1,2,3-trithiin, and 5-methyl-1,2,3,4-tetrathiane. N,N′-Diallylthiourea, which was the major degradation product in the aqueous phase from the thermal reaction of allyl isothiocyanate, was identified by using LC-MS (APCI+), direct-probe EI-MS, and 1H-NMR. The possible mechanism for the formation of these products was proposed.
- Chen, Chung-Wen,Ho, Chi-Tang
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p. 220 - 223
(2007/10/03)
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- BIS(BROMOMAGNESIUM) SULFIDE - A REAGENT FOR THE SYNTHESIS OF DIORGANIC SULFIDES
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Bis(bromomagnesium) sulfide was obtained by the reaction of ethylmagnesium bromide with hydrogen sulfide. In reaction with electrophilic reagents in THF or diethyl ether it gives good yields of symmetrical sulfides with a high degree of purity.
- Nedugov, A. N.,Pavlova, N. N.
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p. 1103 - 1104
(2007/10/02)
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- REACTION OF DIALLYL DISULFIDE WITH ACETYLENE IN THE SUPERBASIC POTASSIUM HYDROXIDE-DMSO SYSTEM
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1-Vinylthio-3-(1-propenylthio)-1-propene, vinyl 1-propenyl sulfide, and 1,2-bis(1-propenylthio)ethene were obtained by the reaction of diallyl disulfide with acetylene in the potassium hydroxide-DMSO system.The effect of the reaction conditions (temperature, time, amount of potassium hydroxide, inhibitors, and the concentration of water in the DMSO) on the yields of the products and the selectivity of the process was investigated.Diallyl sulfide, allyl 1-propenyl sulfide, and di(1-propenyl) sulfide were obtained as side products with an overall yield of about 6percent.
- Amosova, S. V.,Nosyreva, V. V.,Musorin, G. K.,Sigalov, M. V.
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p. 239 - 243
(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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- Bis(tributyltin) Sulfide: An Effective and General Sulfur-Transfer Reagent
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Bis(tributyltin) sulfide acts efficiently to transfer the sulfur atom as S(2-) to a variety of halide substrates to afford the corresponding symmetrical sulfides in good overall yield.
- Harpp, David N.,Gingras, Marc,Aida, T.,Chan, T. H.
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p. 1122 - 1124
(2007/10/02)
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- NUCLEOPHILIC THIYLATION OF ALLYL HALIDES IN THE PRESENCE OF PHASE-TRANSFER CATALYSTS
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A study was carried out on the thiylation of allyl halides by sodium sulfide nonahydrate and 1-butanethiol in the presence of tetrabutylammonium bromide and polyglycol as phase-transfer catalysts leading to the formation of allyl sulfides.The physical constants, spectra characteristics and yields are given for the thiylation products.
- Tolstikov, G. A.,Kanzafarov, F. Ya.,Kanzafarova, S. C.,Singizova, V. Kh.
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p. 1261 - 1266
(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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- Selective Condensation of titanium Reagent with Carbonyl Compounds
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titanium reagent generated easily from allyl ethyl sulfides condensed with aldehydes to give erythro-β-hydroxy sulfides in highly regio- and stereoselective manner.In contrast, crotyl ethyl sulfide reacted with aldehydes affording δ-hydroxy vinyl sulfide exclusively.The substitution pattern of the starting sulfide can have a pronounced effect on the selectivity in this condensation reaction, erythro-β-Hydroxy sulfide obtained was transfromed stereoselectively to the trans-vinyloxirane or 1,3-alkadiene.
- Furuta, Kyoji,Ikeda, Yoshihiko,Meguriya, Noriyuki,Ikeda, Nobuo,Yamamoto, Hisashi
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p. 2781 - 2790
(2007/10/02)
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