- Anodic methoxylation of 2-acyloxy-3,3,3-trifluoropropyl sulfides accompanying with [1,2]-rearrangement of the acyloxy group and anodic cyclization of 2-(t-butoxycarbonyl)oxy-3,3,3-trifluoropropyl sulfide
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Anodic methoxylation of 2-acyloxy-3,3,3-trifluoropropyl sulfides was carried out in methanol containing Et3N-3HF as a supporting electrolyte and mediator using an undivided cell to provide the corresponding α-methoxylated products and unexpecte
- Isokawa, Motoaki,Sano, Masaru,Kubota, Kiyotaka,Suzuki, Katsutoshi,Inagi, Shinsuke,Fuchigami, Toshio
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p. G121 - G127
(2017/11/17)
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- Synthesis and evaluation of sulfonylethyl-containing phosphotriesters of 3′-azido-3′-deoxythymidine as anticancer prodrugs
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A series of bis(sulfonylethyl) and mono(sulfonylethyl) phenyl phosphotriesters of zidovudine (3′-azido-3′-deoxythymidine, AZT) were synthesized as potential anticancer prodrugs that liberate AZT monophosphate via nonenzymatic β-elimination mechanism. Stab
- Wang, Jiang,Wang, Yi-Jun,Chen, Zhe-Sheng,Kwon, Chul-Hoon
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p. 5747 - 5756
(2015/01/09)
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- " On-water " thiolysis of epoxides promoted by PhSZnBr
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The synthesis of a new bench-stable and odorless zinc thiolate is here reported. The thiolysis of epoxides effected using this reagent showed a considerable rate acceleration of the reaction when effected in "on-water" conditions. In addition, the reactio
- Propersi, Simona,Tidei, Caterina,Bagnoli, Luana,Marini, Francesca,Testaferri, Lorenzo,Santi, Claudio
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p. 671 - 676
(2014/01/06)
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- (Bromodimethyl)sulfonium bromide-mediated thiolysis of epoxides: An easy access to -hydroxy sulfides and benzoxathiepinones in solvent-free conditions
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A mild, rapid and highly regioselective opening of epoxides by mercaptans to bη-hydroxy sulfides and benzoxathiepinones has been achieved in excellent yields, using catalytic amount of (bromodimethyl)sulfonium bromide in solvent free reaction conditions.
- Shailaja,Manjula,Rao, B. Vittal
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experimental part
p. 3629 - 3639
(2011/02/22)
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- Efficient synthesis of-Hydroxy sulfides and-Hydroxy sulfoxides catalyzed by Cu/MgO under solvent-free conditions
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Regio-, stereo-, and chemoselective ring opening of epoxides with thiols using Cu/MgO as a heterogeneous catalyst has efficiently been carried out to produce the corresponding β-hydroxy sulfides in excellent yields at room temperature under solvent-free c
- Das, Biswanath,Balasubramanyam, Penagaluri,Krishnaiah, Maddeboina,Veeranjaneyulu, Boyapati,Sudhakar, Dega
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experimental part
p. 2113 - 2121
(2010/08/13)
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- LiOH-catalyzed simple ring opening of epoxides under solvent-free conditions
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LiOH has been found to be a very simple and selective catalyst for the rapid and mild synthesis of β-hydroxy sulfides and β-hydroxyl nitriles by ring opening of epoxides with aromatic, aliphatic, and heterocyclic thiols and trimethylsilyl cyanide at room temperature under solvent free conditions. All the reactions proceeded satisfactorily in short times and afforded the corresponding products in good to excellent yields with high regioselectivity and chemoselectivity under mild reaction conditions. Copyright Taylor & Francis Group, LLC.
- Azizi, Najmedin,Khajeh-Amiri, Alireza,Ghafuri, Hossein,Bolourtchian, Mohammad
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scheme or table
p. 1550 - 1557
(2010/09/06)
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- One-pot synthesis of β-amino/β-hydroxy selenides and sulfides from aziridines and epoxides
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Diaryl disulfides and diselenides undergo facile cleavage on treatment with rongalite (sodium hydroxymethanesulfinate) to generate the corresponding thiolate and selenolate species in situ, which effect the ring opening of aziridines and epoxides in a reg
- Ganesh, Venkataraman,Chandrasekaran, Srinivasan
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experimental part
p. 3267 - 3278
(2010/02/27)
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- Cyanuric chloride: An efficient catalyst for ring opening of epoxides with thiols under solvent-free conditions
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2,4,6-Trichloro-1,3,5-triazine-catalyzed convenient and efficient ring opening of epoxides with thiols under solvent-free conditions is described. Short reaction time, mild reaction conditions, inexpensive and readily available catalyst, and excellent yie
- Bandgar, Babasaheb P.,Joshi, Neeta S.,Kamble, Vinod T.,Sawant, Sanjay S.
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p. 231 - 234
(2008/09/18)
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- Stereo- and regioselective thiolysis of 1,2-epoxides in water
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A simple, efficient, stereoselective, and highly regioselective procedure for the synthesis of β-hydroxy sulfides by thiolysis of various 1,2-epoxides in water as a solvent, using no catalyst and under very mild conditions, is described. Copyright Taylor
- Movassagh, Barahman,Soleiman-Beigi, Mohammad
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p. 3239 - 3244
(2008/02/12)
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- Regioselective reaction of epoxides with disulfides using Zn/AlCl 3 system: A simple synthesis of β-hydroxy sulfides
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Epoxides are regioselectively cleaved by zinc thiolate intermediate, generated from disulfides in the presence of Zn/AlCl3 system, to afford high yields of the corresponding β-hydroxy sulfides.
- Movassagh,Sobhani,Kheirdoush,Fadaei
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p. 3103 - 3108
(2007/10/03)
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- Tetrathiomolybdate assisted epoxide ring opening with masked thiolates and selenoates: Multistep reactions in one pot
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Tetrathiomolybdate provides an easy access to β-hydroxy disulfides, β-hydroxy sulfides, and selenides from epoxides in a tandem, multistep process in one pot. This strategy has been utilized effectively in the construction of thiabicylo[3.2.2]nonane derivative 24.
- Devan, Naduthambi,Sridhar, Perali Ramu,Prabhu, Kandikere Ramaiah,Chandrasekaran, Srinivasan
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p. 9417 - 9420
(2007/10/03)
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- Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent- and halogen-free conditions
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Aromatic and aliphatic sulfides are oxidized to sulfoxides or sulfones in high yield with 30% hydrogen peroxide under organic solvent- and halogen-free conditions. Dialkyl and alkyl aryl sulfides are cleanly oxidized to sulfoxides using aqueous hydrogen peroxide without catalysts. The best catalyst for the sulfone synthesis consists of sodium tungstate, phenylphosphonic acid, and methyltrioctylammonium hydrogensulfate. Co-existing primary or secondary alcohol or olefinic moieties are unaffected under such conditions.
- Sato, Kazuhiko,Hyodo, Mamoru,Aoki, Masao,Zheng, Xiao-Qi,Noyori, Ryoji
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p. 2469 - 2476
(2007/10/03)
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- Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides: Versatile synthons for enantiopure β-hydroxy sulfoxides
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Humicola lanuginosa lipase-catalyzed acylation of β-hydroxy sulfides provides both the (R)- and (S)-enantiomers in high enantiomeric purity. In two cases the resolved hydroxy sulfides were oxidized to give β-hydroxy sulfoxides in >99% e.e. The effect of substituents on enantioselectivity is discussed.
- Singh, Satwinder,Kumar, Subodh,Chimni, Swapandeep Singh
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p. 2457 - 2462
(2007/10/03)
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- Convenient preparation of ytterbium(III) chalcogenolate complexes by insertion of ytterbium into chalcogen-chalcogen bonds. Application in the ring-opening of epoxides
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Convenient conditions are reported for the preparation of ytterbium(III) chalcogenolate complexes by insertion of ytterbium metal into the chalcogen- chalcogen bond of disulfides, diselenides, and ditellurides. The resulting complexes have been found to t
- Dowsland, Jennifer,McKerlie, Fiona,Procter, David J.
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p. 4923 - 4927
(2007/10/03)
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- Facile synthesis of vinyl sulfones from β-bromo alcohols
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Vinyl sulfones are synthesized in good yields by dehydration of β- hydroxy sulfones derived from β-bromo alcohols.
- Lee, Jae Wook,Lee, Chi-Wan,Jung, Jin Hang,Oh, Dong Young
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p. 2897 - 2902
(2007/10/03)
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- Polyethylene Glycol (PEG) 4000 Catalysed Regioselective Nucleophilic Ring Opening of Oxiranes - A New And Convenient Synthesis of β-Hydroxy Sulfone and β-Hydroxy Sulfide
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Oxiranes and sodium p-toluene sulfinate salt react smoothly in a regioselective manner in the presence of PEG4000 to furnish β-hydroxy sulfone and β-hydroxysulfide.The reaction was extended for the preparation of alkylsulfones and β-oxosulfones from alkylhalide and β-oxohalide respectively.
- Maiti, A. K.,Bhattacharyya, P.
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p. 10483 - 10490
(2007/10/02)
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- NEW ROUTE TO THE PREPARATION OF 1,3,2 OXATHIAPHOSPHOLANES 2-SULFIDE DERIVATIVES
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5-Substituted 2-alkyl (or aryl, heteroaryl,...)thio 1,3,2 oxathiaphospholanes 2-sulfide 5 are readily accessible by reaction of the triethylammonium salt 1 of a diester of the phosphorotetrathioic acid with appropriate epoxide in the presence of BF3*Et2O as catalyst.
- Comel, Alain,Kirsch, Gilbert,Paquer, Daniel
-
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- Highly Regioselective and Stereospecific Functionalization of 1,2-Proanediol with Trimethyl(X)silanes Employing the 1,3,2λ5-Dioxaphospholane Methodology
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The regioselective ring opening of (S)-4-methyl-2,2,2-triphenyl-1,3,2λ5-dioxaphospholanes (2) was initiated with several trimethylsilyl reagents (Me3SiX: X = PhS, I, Br; Cl, CN, and N3) to afford the regioisomeric (silyloxy)phosphonium salts.A stereospecific extrusion of triphenylphosphine oxide from these oxyphosphonium salts gave predominatly the thermodynamically less stable C-2-X-substituted derivatives with nearly complete inversion of stereochemistry at the C-2 stereogenic center (i.e., X = PhS).
- Mathieu-Pelta, Isabel,Evans, Slayton A.
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p. 3409 - 3413
(2007/10/02)
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- SYNTHESIS OF 1,3,2-OXATHIAPHOSPHOLANE-2-SULFIDE DERIVATIVES
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5-Substituted 2-alkyl (or aryl, heteroaryl, ...)thio-1,3,2-oxathiaphospholane-2-sulfides 5 are readily accessible by reaction of the triethylammonium salt 1 of a diester of the phosphorotetrathioic acid with appropriate epoxides in the presence of BF3/Et2O as catalyst.Key words: BF3/Et2O; cyclisation reaction; NMR; oxathiaphospholane derivatives; oxiranes; phosphorotetrathioic acid; triethylammonium salts.
- Comel, Alain,Kirsch, Gilbert,Paquer, Daniel
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p. 229 - 234
(2007/10/02)
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- Cobalt mediated regioselective ring opening of oxiranes with benzenethiol: A mechanistic study
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: Oxiranes are regioselectively cleaved by benzenethiol in presence of cobalt(II) chloride or Co2(CO)8 to the corresponding β-hydroxy sulfides in good yields. A mechanistic study of this reaction reveals that an electron transfer process is involved in these transformations and the reaction is proceeding via the formation of a carbon-cobalt bond.
- Iqbal, Javed,Pandey, Anu,Shukla, Alka,Srivastava, Rajiv Ranjan,Tripathi, Sanjay
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p. 6423 - 6432
(2007/10/02)
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- Switching of the Direction of Enzyme-Mediated Oxidation and Reduction of Sulfur-Substituted 2-Propanols and 2-Propanones
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Incubation of 1-(phenylsulfenyl)-2-propanone with Corynebacterium equi IFO 3730 grown on hexadecane at pH 6.5 afforded the corresponding 1-substituted S propanols. 1-(Phenylsulfinyl)-2-propanone was also reduced by the microorganism, the product being aff
- Ohta, Hiromichi,Kato, Yasuo,Tsuchihashi, Gen-ichi
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p. 2735 - 2739
(2007/10/02)
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- O-SILYLATED ENOLATE PHENYLTHIOALKYLATION: a SYNTHESIS OF α,β-UNSATURATED 5- AND 6-MEMBERED LACTONES.
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ZnBr2-catalysed phenylthioalkylation of keten bis(trimethylsilyl)acetals, obtained from carboxylic acids, with appropriate α-chlorosulphides can be used to prepare γ- and δ-lactones.
- Khan, Hassan A.,Paterson, Ian
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p. 5083 - 5084
(2007/10/02)
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