- Silica gel-supported polyphosphoric acid (PPA/SiO2) as an efficient and reusable catalyst for conversion of carbonyl compounds into oxathioacetals and dithioacetals
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A simple and efficient method for the conversion of carbonyl compounds to oxathioacetals and dithioacetals by using polyphosphoric acid supported on silica gel (PPA/SiO2) as an acid catalyst have been developed. PPA/SiO2 is easily re
- Aoyama, Tadashi,Takido, Toshio,Kodomari, Mitsuo
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- Palladium-Catalyzed Synthesis of Aryl Vinyl Sulfides via 1,3-Oxathiolanes As Vinyl Sulfide Surrogates
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A nontraditional approach to synthesizing aryl vinyl sulfides is described. 2,2-Diphenyl-1,3-oxathiolane slowly liberates a vinyl sulfide anion under basic conditions. Using a Pd/Xantphos catalyst system to activate a wide range of aryl bromides, this transient sulfide species can be effectively trapped and fed into a traditional Pd0/PdII catalytic cycle. Scope and limitations of the methodology are presented along with significant discussion of a competitive C-S bond activation by this catalyst system.
- Schmink, Jason R.,Dockrey, Summer A. Baker,Zhang, Tianyi,Chebet, Naomi,Van Venrooy, Alexis,Sexton, Mary,Lew, Sarah I.,Chou, Steffany,Okazaki, Ami
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supporting information
p. 6360 - 6363
(2016/12/23)
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- Facile protection of carbonyl compounds as oxathiolanes and thioacetals promoted by PEG1000-based dicationic acidic ionic liquid as chemoselective and recyclable catalyst
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Efficient oxathioacetalization and thioacetalization of carbonyl compounds have been achieved in high yields employing PEG1000-based dicationic acidic ionic liquid as a catalyst. The PEG ionic liquid and toluene have the advantages of both homo
- Ren, Yi-Ming,Shao, Juan-Juan,Wu, Zhi-Chuan,Zhang, Shuai,Tao, Ting-Xian
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p. 392 - 394
(2014/06/09)
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- Silica-gel supported sulfamic acid (SA/SiO2) as an efficient and reusable catalyst for conversion of ketones into oxathioacetals and dithioacetals
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A simple and efficient method for the conversion of carbonyl compounds to oxathioacetals and dithioacetals using SA/SiO2 as an acid catalyst has been achieved. SA/SiO2 is easily recovered from the reaction mixture and can be reused at least 15 times without loss of catalytic activity.
- Aoyama, Tadashi,Suzuki, Toshihiko,Nagaoka, Takashi,Takido, Toshio,Kodomari, Mitsuo
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p. 553 - 566
(2013/01/15)
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- An efficient and mild deprotection of 1,3-oxathiolanes to carbonyl compounds using the superoxide ion
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An efficient deprotection of 1,3-oxathiolanes to carbonyl compounds has been achieved under the mild reaction conditions of tetraethylammonium superoxide in an aprotic medium at room temperature.
- Singh, Satish Kumar,Singh, Krishna Nand
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body text
p. 2339 - 2343
(2010/03/26)
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- Facile protection of carbonyl compounds as oxathiolanes and transoxathioacetalization of oxyacetals promoted by iron(III) trifluoroacetate or trifluoromethanesulfonate as chemoselective and recyclable catalysts
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Oxathioacetalization of carbonyl compounds and transoxathioacetalization of O,O-acetals/ketals are reported under nearly neutral conditions promoted by iron(III) trifluoroacetate [Fe(CF3CO2)3] or trifluoromethanesulfonate
- Adibi, Hadi,Jafari, Hadi
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p. 679 - 682
(2008/01/01)
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- An efficient and chemoselective method for conversion of carbonyl compounds to 1,3-oxathiolanes with 2-mercaptoethanol catalyzed by TiCl 4-montmorillonite
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Formation of 1,3-oxathiolanes from aldehydes and ketones using 2-mercaptoethanol in the presence of TiCl4-montmorillonite under mild reaction conditions in excellent yields is described. Chemoselective monothioacetalization of aldehyde in the p
- Jin, Tong-Shou,Zhao, Rui-Qiao,Ma, Yan-Ran,Yang, Mi-Na,Guo, Jun-Jie,Li, Tong-Shuang
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p. 503 - 505
(2007/10/03)
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- Mild and efficient method for oxathioacetalization of carbonyl compounds
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An efficient procedure for the protection of carbonyl compounds into the corresponding 1,3-oxathioacetal has been achieved using PAS as catalyst. Copyright Taylor & Francis Group, LLC.
- Majee, Adinath,Kundu, Shrishnu Kumar,Islam, Samimul
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p. 3767 - 3770
(2007/10/03)
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- Microwave-mediated efficient protection of carbonyl compounds as 1,3-oxathiolanes in the presence of iodine under solvent free condition
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A mild, efficient, and solvent free protocol for conversion of aldehydes and ketones into their corresponding 1,3-oxathiolanes using 2-mercaptoethanol in the presence of catalytic amount of elemental iodine is reported. Copyright
- Bez, Ghanashyam,Baruah, Nabajyoti
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p. 542 - 543
(2007/10/03)
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- Ytterbium(III) triflate-catalyzed conversion of carbonyl compounds into 1,3-oxathiolanes in ionic liquids
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The reaction of carbonyl compounds with 2-mercapto-ethanol to prepare 1,3-oxathiolanes has been successfully carried out in ionic liquids using ytterbium(III) triflate as a catalyst. Yields of the products are high and the catalyst can be easily recovered
- Kumar, Anil,Jain, Nidhi,Rana, Sandeep,Chauhan, Shive M. S.
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p. 2785 - 2787
(2007/10/03)
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- Mild and efficient iodine catalyzed protection of carbonyl compounds as oxathiolane derivatives
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A number of aldehydes and ketones have been protected as their corresponding 1,3-oxathiolane derivatives with 2-mercaptoethanol using catalytic amount of molecular iodine.
- Rana,Guin,Banerjee,Roy
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p. 1005 - 1006
(2007/10/03)
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- Scandium(III) Triflate as an Efficient and Recyclable Catalyst for Chemoselective Conversion of Carbonyl Compounds to 1,3-Oxathiolanes
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A variety of carbonyl compounds can be easily and rapidly converted to the corresponding 1,3-oxathiolanes in the presence of a catalytic amount of scandium(III) triflate [Sc(OTf)3] in CH2Cl2. After completion of the reacti
- Karimi, Babak,Ma'mani, Leila
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p. 2503 - 2506
(2007/10/03)
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- A useful and convenient synthetic protocol for interconversion of carbonyl compounds to the corresponding 1,3-oxathiolanes and vice versa employing organic ammonium tribromide (OATB)
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A wide variety of carbonyl compounds 1 can be easily protected selectively as the corresponding 1,3-oxathiolanes 2 in good yields using a catalytic amount (0.01-0.1 equiv.) of n-tetrabutylammonium tribromide in dry CH2Cl2 at 0-5°C. O
- Mondal, Ejabul,Sahu, Priti Rani,Bose, Gopal,Khan, Abu T.
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p. 2843 - 2846
(2007/10/03)
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- 2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS) and bromine as efficient catalysts for dithioacetalization and oxathioacetalization of carbonyl compounds and transdithioacetalization reactions
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The use of 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS), and bromine as efficient catalysts for conversion of carbonyl compounds to their cyclic and acyclic dithioacetals and 1,3-oxathiolanes under mild reaction conditions are described. These catalysts are also used for efficient transdithioacetalization of acetals, diacetals, ketals, acylals, enamines, hydrazones, and oximes with high yields in the presence of thiols.
- Iranpoor, Nasser,Firouzabadi, Habib,Shaterian, Hamid Reza,Zolfigol
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p. 1047 - 1071
(2007/10/03)
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- Indium trifluoromethanesulfonate as a mild and chemoselective catalyst for the conversion of carbonyl compounds into 1,3-oxathiolanes
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An efficient method for the preparation of 1,3-oxathiolanes from aldehydes and ketones with 2-mercaptoethanol in the presence of a catalytic amount of indium trifluoromethanesulfonate is reported.
- Kazahaya, Kiyoshi,Hamada, Nao,Ito, Shinya,Sato, Tsuneo
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p. 1535 - 1537
(2007/10/03)
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- Zirconium tetrachloride (ZrCl4) as an efficient and chemoselective catalyst for conversion of carbonyl compounds to 1,3-oxathiolanes
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Different types of aldehydes and ketones can be efficiently converted into their corresponding 1,3-oxathiolanes using 2-mercaptoethanol (1.5-3.2 equiv.) in the presence of catalytic amount (0.04-0.15 equiv.) of ZrCl4 in CH2Cl2/
- Karimi, Babak,Seradj, Hassan
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p. 805 - 806
(2007/10/03)
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- Selective Catalytic Transesterification, Transthiolesterification, and Protection of Carbonyl Compounds over Natural Kaolinitic Clay
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Transesterification and transthiolesterification of β-keto esters with variety of alcohols and thiols and selective protection of carbonyl functions with various protecting groups catalyzed by natural kaolinitic clay are described. The clay has been found to be an efficient catalyst in transesterifying long chain alcohols, unsaturated alcohols, and phenols to give their corresponding β-keto esters in high yields. For the first time, transthiolesterification of β-keto esters with a variety of thiols has been achieved under catalytic conditions. Clay also catalyzes selective transesterification of β-keto esters by primary alcohols in the presence of secondary and tertiary alcohols giving corresponding β-keto esters. A systematic study involving the reactivity of different nucleophiles (alcohols, amines, and thiols) toward β-keto esters is also described. Sterically hindered carbonyl groups as well as α,β-unsaturated carbonyl groups underwent protection without the deconjugation of the double bond. Chemoselective protection of aldehydes in the presence of ketones has also been achieved over natural kaolinitic clay.
- Ponde, Datta E.,Deshpande, Vishnu H.,Bulbule, Vivek J.,Sudalai, Ammugam,Gajare, Anil S.
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p. 1058 - 1063
(2007/10/03)
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- A silver salt - iodine reagent system for the deprotection of monothioacetals and dithioacetals
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A new reagent (silver salt - iodine) system was developed for the deprotection of monothioacetals and dithioacetals. The reactions using this reagent system afforded the parent carbonyl compounds in moderate to quantitative yields under mild conditions. T
- Nishide, Kiyoharu,Nakamura, Daisaku,Yokota, Kouichi,Sumiya, Toshio,Node, Manabu,Ueda, Masaru,Fuji, Kaoru
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p. 393 - 404
(2007/10/03)
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- Interconversion of oxathiolanes and carbonyls under essentially identical conditions
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A catalytic, non-aqueous protocol for the interconversion of oxathiolanes and carbonyl compounds at room temperature is described.
- Ravindranathan,Chavan, Subhash P.,Dantale, Shubhada W.
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p. 2285 - 2288
(2007/10/02)
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- Fungal biotransformation of 1,3-oxathiolanes
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A series of 2,2-disubstituted 1,3-oxathiolanes has been incubated with fungi known to be capable of efficient asymmetric oxidation of sulfides to sulfoxides.In three cases (2-phenyl-1,3-oxathiolane, 2-methyl-2-phenyl-1,3-oxathiolane, and 2-tert-butyl-2-phenyl-1,3-oxathiolane), sulfoxidation occured to give a single diastereomer of sulfoxide, whose relative stereochemistry has been assigned by 1H nuclear magnetic resonance analysis.The sulfoxides were obtained as racemates or had low enantiomeric enrichment.In some cases ketones, assumed to be formed by spontaneous hydrolysis of oxathiolane sulfoxides, were obtained, together with their reduction products, secondary alcohols.
- Holland, Herbert L.,Munoz, Benito
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p. 2299 - 2303
(2007/10/02)
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- A New Ready, High-Yielding, General Procedure for Acetalization of Carbonyl Compounds
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Carbonyl compounds are smoothly and rapidly acetalized by treatment with alcohols, in anhydrous acetonitrile, in the presence of polystyryl diphenyl phosphine - iodine complex as catalyst.Open and cyclic acetals, including 1,3-dioxolanes, 1,3-oxathiolanes, and 1,3-dithiolanes, of miscellaneous aldehydes and ketones have been successfully prepared in this way.The isolation of the product is very easily performed, by simple filtration of the polymer-linked phosphine oxide which is formed in the reaction.
- Caputo, Romualdo,Ferreri, Carla,Palumbo, Giovanni
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p. 386 - 389
(2007/10/02)
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- A Kinetic Study of the Soft Metal Ion-promoted Hydrolyses of Some S-Acetals
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The S-acetals (III)-(VII) hydrolyse readily in aqueous ethanol or in aqueous dioxan solutions containing an excess of Tl3+ or Ag+ ions to give benzophenone and the appropriate sulphide.The hydrogen-ion catalysed hydrolyses are very slow by comparison and the supposedly soft ions Cd2+ and Cu2+ have even less effect than H3O+.Kinetic and spectroscopic studies of the hydrolyses, mainly at 25 deg C, show that the Tl3+-promoted reactions occur via the rapid formation of a 1 Tl3+ : 1-S-acetal adduct.This adduct is formed stoicheiometrically with (IV), (V), and(VII), but in small amounts with (III) and (VI).The tripositive adduct probably reacts with water in the slow step of the overall hydrolysis.This adduct can also lose charge by proton dissociation from hydroxy groups in the bound S-acetal, or from thallium-bound water.The resulting dipositive adducts, however formed, hydrolyse much less rapidly than the tripositive adducts.The (chelated) dipositive adduct from (V) is sufficiently stable for contributions to hydrolysis from a 4+ adduct to be detected.The Ag+-promoted hydrolyses proceed principally via small amounts of rapidly formed dipositive 2 Ag+ : 1-S-acetal adducts.For (V), where loss of a carboxy proton can occur, the formation constant of the monopositive + adduct is very large (K ca. 107 l mol-1) but that of the dipositive adduct is small, as for the other S-acetals.With (V) and (VI) the 1 Ag+ : 1-S-acetal adduct is formed stoicheiometrically and with (IV) its formation constant is large (K ca, 900 l mol-1).For (III), (IV), (VI), and (VII) these 1:1 adducts contribute significantly to the hydrolysis at low silver ion concentrations.For both the Tl3+-and the Ag+-promoted reactions the effects of ionic strength are consistent: where more charged adduct can form an increase in ionic strength increases the reaction rate; where adduct formation is complete, changes in ionic strength have little effect on the rate.The S-acetals display wide (up to 105-fold) differences in reactivity towards hydrolysis and their sequence of reactivity alters markedly with the promoting ion.With both ions (VI) hydrolyses relatively slowly.For all the substrates Tl3+ is a better promoter than Ag+.Exact comparisons of reactivity are impossible owing to the differences in mechanistic detail and in solvent.In view of its soft acid character Tl3+ is surprisingly more acidic towards the O-containing acetals than towards those having just two S atoms.For (IV) and Ag+ the establishment of the pre-equilibrium giving the 1 Ag+ : 1-S-acetal adduct is slow enough at 25 deg C to be followed by stopped-flow spectroscopy.
- Satchell, Derek P. N.,Weil, Thomas J.
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p. 1191 - 1200
(2007/10/02)
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