- Blue LED-Promoted Oxathiacetalization of Aldehydes and Ketones
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In synthetic chemistry, the protection of aldehydes and ketones is crucial during multistep synthesis of complex molecules. Organic chemists have paid substantial attention to the synthesis of 1,3-oxathiolanes and 1,3-oxathianes because of their considera
- Liu, You-Chen,Reddy, Daggula Mallikarjuna,Chen, Xin-An,Shieh, Yi-Chen,Lee, Chin-Fa
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p. 2542 - 2552
(2020/04/27)
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- Selective arylthiolane deprotection by singlet oxygen: A promising tool for sensors and prodrugs
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A routine thioketal protecting group reacts rapidly and selectively with singlet oxygen to reveal ketone products in good (aryl 1,3-dithiolane) to excellent (aryl 1,3-oxathiolane) yields. Arylthiolanes are stable to biologically relevant reactive oxygen species and can be used as a light-activated gating mechanism for activating fluorescent sensors or small molecule prodrugs.
- Lamb, Brian M.,Barbas, Carlos F.
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supporting information
p. 3196 - 3199
(2015/05/27)
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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 method for the oxathioacetalization of carbonyl compounds using N-bromosaccharin as a catalyst
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A mild and highly chemoselective method for the preparation of oxathiolane from aliphatic and aromatic aldehydes and ketones with 2-mercaptoethanol in the presence of catalytic amount of N-bromosaccharin at room temperature is reported.
- Alinezhad, Heshmatollah,Fallahi, Shahrouz
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experimental part
p. 927 - 929
(2012/08/28)
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- Catalytic carbon-sulfur bond formation by amphoteric vanadyl triflate: exploring with thia-Michael addition, thioacetalization, and transthioacetalization reactions
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A series of thiols have been examined as protic nucleophiles for Michael-type additions to α,β-unsaturated carbonyls as well as double nucleophilic condensations with aldehydes, ketones, and acetals catalyzed by amphoteric, water-tolerant vanadyl triflate under mild and neutral conditions. The newly developed C-S bond formation protocols were carried out smoothly in good to high yields in a highly chemoselective manner.
- Chen, Chien-Tien,Lin, Yow-Dzer,Liu, Cheng-Yuan
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supporting information; experimental part
p. 10470 - 10476
(2010/02/28)
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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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- 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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- Silica-supported perchloric acid (HClO4-SiO2): A versatile catalyst for tetrahydropyranylation, oxathioacetalization and thioacetalization
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A simple and convenient synthetic protocol for the protection of hydroxyl group as tetrahydropyranyl ether as well as carbonyl functionality as oxathioacetal and thioacetal has been achieved using a catalytic amount of silica-supported perchloric acid und
- Khan, Abu T.,Parvin, Tasneem,Choudhury, Lokman H.
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p. 2497 - 2502
(2008/02/03)
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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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- Tantalum(V) chloride-silica gel: An efficient catalyst for conversion of carbonyl compounds to 1,3-oxathiolanes
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A variety of carbonyl compounds can be easily converted to the corresponding 1,3-oxathiolanes in the presence of a catalytic amount of tantalum(V) chloride [TaCl5] on silica gel in dichloromethane. Mild reaction conditions, efficiency, high yie
- Chandrasekhar,Prakash, S. Jaya,Shyamsunder,Ramachandar
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p. 3127 - 3131
(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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- Deprotection of 1,3-oxathiolanes to carbonyl compounds with montmorillonite K10
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Montmorillonite K10 has been used in the deprotection of different aromatic and aliphatic 1,3-oxathiolanes to the corresponding carbonyl compounds in 73 to 97% yields under mild and environmentally compatible conditions.
- Chauhan,Kumar, Anil,Sahoo
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p. 2635 - 2637
(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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- 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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- 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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- Ceric ammonium nitrate as a convenient catalyst for protection of carbonyl compounds as 1,3-oxathianes
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A mild and efficient method for the protection of carbonyl compounds as 1,3-oxathianes has been established by the catalytic use of ceric ammonium nitrate at ambient temperature. While different types of aryl and alkyl ketones and aldehydes were protected
- Maiti, Gourhari,Roy, Subhas Chandra
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p. 2269 - 2273
(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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- 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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- A useful and catalytic method for protection of carbonyl compounds into the corresponding 1,3-oxathiolanes and deprotection to the parent carbonyl compounds
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A wide variety of carbonyl compounds 1 can be easily protected to the corresponding 1,3-oxathiolanes 2 in good yields in the presence of catalytic amount of perchloric acid in dry CH2Cl2 at 0-5 °C. On the other hand, various 1,3-oxathiolanes 2 can be selectively deprotected to the parent carbonyl compounds 1 in very good yields by H2MoO4·H2O-H2O2 catalyzed oxidation of ammonium bromide in the presence of perchloric acid in CH2Cl2-H2O solvent system. Mild reaction condition, high selectivity, efficient and relatively good yields are some of the major advantages of the procedure.
- Mondal, Ejabul,Sahu, Priti Rani,Khan, Abu T.
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p. 463 - 467
(2007/10/03)
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- Thioacetalization of aldehydes and ketones in the presence of hydroxo complexes of platinum(II): An example of Lewis acid catalytic activity
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The complex [(dppb)Pt(μ-OH)]2(BF4)2 displays high catalytic activity in the thioacetalization of a variety of aldehydes and ketones with mercaptoethanol under very mild conditions. The reaction rate is greatly enhanced by
- Battaglia,Pinna,Strukul
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p. 621 - 625
(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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- 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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- ENANTIOSELECTIVE OXIDATION OF CYCLIC DITHIOACETALS AND DITHIOKETALS
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The asymmetric oxidation of a series of dithio acetals and dithio ketals to their corresponding monosulphoxides by the procedure developed in our laboratory has been carried out.Simple 1,3-dithiolanes pr
- Furia, Fulvio Di,Licini, Giulia,Modena, Giorgio
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p. 165 - 170
(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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- Electron Impact Induced Fragmentations of Some 2,2-disubstituted 1,3-oxathiolanes
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The electron impact induced fragmentations of nine 2,2-disubstituted 1,3-oxathiolanes have been studied by means of exact mass measurement and metastable ion analysis.The ring cleavage almost always takes place so that the C(2)-S and C(5)-O bonds are brok
- Vainiotalo, Pirjo,Nevalainen, Vesa
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p. 467 - 472
(2007/10/02)
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- Comparative radioprotective activity of various pentagonal compounds with two heteroatomes
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Various heterocyclic compounds with two heteroatomes were synthesized and their potential radioprotective activity was tested. This study shows the interest of phenylthiazolidines derivatives in chemical radioprotection.
- Robbe,Fernandez,Dubief,et al.
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p. 235 - 243
(2007/10/02)
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- The Reaction of 2-Ethoxy-1,3-oxathiolane with Carbonyl Compounds in the Presence of ZnCl2 or HgCl2
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In the reaction of 2-ethoxy-1,3-oxathiolane with carbonyl compounds in the presence of ZnCl2 or HgCl2, it has been found that only the breaking of the endocyclic bond (C-O or C-S bond) occurs, while the breaking of the exocyclic C-O bond to give the 1,3-o
- Tanimoto, Shigeo,Jo, Shigeo,Sugimoto, Toyonari,Okano, Masaya
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p. 3237 - 3238
(2007/10/02)
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- Sulfur Heterocycles. 3. Heterogeneous, Phase-Transfer, and Acid-Catalyzed Potassium Permanganate Oxidation of Sulfides to Sulfones and a Survey of their Carbon-13 Nuclear Magnetic Resonance Spectra
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Although numerous oxidation methods are available for the transformation of sulfides into sulfones, low-molecular-weight, heterocyclic sulfides are often not amenable to this oxidation techniques.The method presented here is a general and economical oxidation using potassium permanganate and various catalysts.Nineteen low-molecular-weight and heterocyclic sulfides were successfully oxidized by variations of this technique, and the results are presented here.In addition, the carbon-13 NMR spectra of these compounds and about two dozen others are reported.General chemical shift trends are reported for selected compounds, and details can be found in the supplementary material.
- Gokel, George W.,Gerdes, Harold M.,Dishong, Dennis M.
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p. 3634 - 3639
(2007/10/02)
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