- 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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- 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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- Nickel(II) chloride hexahydrate catalyzed reaction of aromatic aldehydes with 2-mercaptoethanol: Formation of supramolecular helical assemblage of the product
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Various aromatic aldehydes on reaction with 2-mercaptoethanol provided an unanticipated product, bis(2-hydroxyethyl)dithioacetals (3) as the major product along with the expected product 1,3-oxathiolanes (4) in the presence of 0.05 equiv amount of nickel(
- Laskar, Rajibul A.,Begum, Naznin A.,Mir, Mohammad Hedayetullah,Rohman, Md. Rumum,Khan, Abu T.
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p. 5839 - 5844
(2013/10/21)
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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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- Helical Al- and Ce-MCM-41 materials as novel catalyst for acid and redox processes
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Helical mesoporous silicas containing aluminium or cerium into their framework have been synthesized via hydrothermal method. The synthesized materials were extensively characterized to understand their physico-chemical properties in view of their future catalytic applications. Low-angle powder XRD patterns of calcined samples showed a hexagonally ordered mesopore structure. NMR spectra of aluminium materials exhibited two signals at 50 and 0 ppm assigned to tetracoordinated and octahedrally coordinated Al3+. DR-UV-vis and XPS spectrum of cerium content materials show that cerium was incorporated as Ce3+ and Ce4+ into the helical mesoporous material. Materials with molar ratios Si/Al = 95 and Si/Ce = 500 were found to be catalytically active in acid (oxathioacetalisations and alkylations) or redox (epoxidation of cyclohexene) catalyzed processes, respectively.
- Carrillo, Adela I.,Serrano, Elena,Serrano-Ruiz, Juan Carlos,Luque, Rafael,Garcia-Martinez, Javier
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scheme or table
p. 1 - 9
(2012/10/18)
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- Efficient procedure for oxathioacetalization using the novel ionic liquid
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The novel ionic liquid with multi-SO3H groups has been synthesized through the simple procedure and its catalytic activity for the oxathioacetalization was investigated carefully at room temperature under solvent-free condition. The results sho
- Bao, Shaohua,Chen, Lu,Ji, Yongjun,Yang, Jianguo
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experimental part
p. 2119 - 2122
(2011/10/03)
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- Introducing catalytic activity in helical nanostructures: Microwave assisted oxathioacetalisation catalysed by Al-containing helical mesoporous silicas
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Al-containing helical mesoporous silicas have been synthesized and characterised by different techniques, showing outstanding activities (comparable to those obtained with sulfuric acid) in the oxathioacetalization of cyclohexane. The Royal Society of Che
- Carrillo, Adela I.,Serrano, Elena,Luque, Rafael,Matinez, Javier Garcia
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scheme or table
p. 5163 - 5165
(2010/10/19)
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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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- Chemoselective dithioacetalization and oxathioacetalization of carbonyl compounds using alumina sulfuric acid as catalyst
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Carbonyl compounds have been successfully converted into their corresponding dithiolane, dithiane, and oxathiolane derivatives using a catalytic amount of alumina sulfuric acid (Al2O3-SO3H) with excellent yields at room temperature in short reaction times under mild conditions. This simple method is a highly chemoselective procedure for protection of aldehydes in the presence of ketones, and the heterogeneous catalyst can be recovered and reused several times without any loss of its activity. Copyright Taylor & Francis Group, LLC.
- Shaterian, Hamid Reza,Hosseinian, Asghar,Ghashang, Majid
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experimental part
p. 4097 - 4106
(2009/04/11)
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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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- Use of sulfur containing initiators for anionic polymerization of monomers
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An initiator is presented for anionically polymerizing monomers, to provide a functional head group on the polymer. A polymer having a functional head group derived from a sulfur containing anionic initiator, and optionally as additional functional group resulting from the use of a functional terminating reagent, coupling agent or linking agent is also provided. A method is presented for anionically polymerizing monomers comprising the step of polymerizing the monomers with a sulfur containing anionic initiator to provide a functional head group on the polymer. An elastomeric compound, comprising a functional polymer and filler is also described. Also provided is a tire having decreased rolling resistance resulting from a tire component containing a vulcanizable elastomeric compound.
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- Iron(III) fluoride: A highly efficient and versatile catalyst for the protection of carbonyl compounds under solvent-free conditions
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Carbonyl compounds are successfully converted into oxathioacetals and dithioacetals with 2-mercaptoethanol and ethane-1,2-dithiol using a catalytic amount of iron(m) fluoride under solvent-free conditions. The catalysts were recovered and reused in variou
- Bandgar, Babasaheb P.,Kamble, Vinod T.,Kulkarni, Ashwini
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p. 607 - 610
(2007/10/03)
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- 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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p. 2307 - 2310
(2007/10/03)
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- Organic reactions in aqueous media: I2-in-water-catalysed rapid and chemoselective oxathioacetalisation of aldehydes under mild conditions
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I2 in water is found to be an efficient catalyst for the chemoselective protection of both aliphatic and aromatic aldehydes as 1,3-oxathioacetals under mild conditions. Fast reactions and excellent yields of pure products using an inexpensive a
- Bandgar,Bettigeri, Sampada V.
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p. 389 - 391
(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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- Montmorillonite K-10 clay as an efficient solid catalyst for chemoselective protection of carbonyl compounds as oxathiolanes with 2-mercaptoethanol
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Montmorillonite K-10 clay has been found to be a mild and efficient solid catalyst for the protection of a variety of carbonyl compounds, such as oxathiolanes, with 2-mercaptoethanol in good to excellent yields. In addition, by using this catalyst, high chemoselective protection of aldehydes in presence of ketones has been achieved.
- Gogoi, Siddhartha,Borah, Jagat C.,Barua, Nabin C.
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p. 1592 - 1594
(2007/10/03)
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- Pr(OTf)3 as an efficient and recyclable catalyst for chemoselective thioacetalization of aldehydes
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Praseodymium triflate has been found to be an efficient and recyclable catalyst for chemoselective protection of aldehydes.
- De, Surya Kanta
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p. 2837 - 2840
(2007/10/03)
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- Yttrium triflate as an efficient and useful catalyst for chemoselective protection of carbonyl compounds
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Carbonyl compounds have been successfully converted into their corresponding oxathiolane, dithiolane, and dithiane derivatives with 2-mercaptoethanol, 1,2-ethanedithiol, and 1,3-propanedithiol using catalytic amount of yttrium triflate. In addition, by us
- De, Surya Kanta
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p. 2339 - 2341
(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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- Eco-friendly and Highly Chemoselective 1,3-Oxathio- and 1,3-Dithioacetalization of Aldehydes Using Ionic Liquids
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Room temperature ionic liquids have been employed for the first time as novel and recyclable reaction media for the chemoselective conversion of aldehydes into their corresponding 1,3-oxathio- and dithioacetal derivatives in excellent yields under mild an
- Yadav,Reddy,Kondaji
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p. 672 - 673
(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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- A mild and efficient method for the protection of carbonyl compounds as oxathiolanes, dithiolanes and dithianes catalyzed by molybdenyl acetylacetonate
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Carbonyl compounds have been successfully converted into their corresponding oxathiolane, dithiolane and dithiane derivatives in excellent yields with 2-mercaptoethanol, 1,2-ethanedithiol and 1,3-propanedithiol using a catalytic amount of molybdenyl acety
- Rana, Kalyan Kumar,Guin, Chandrani,Jana, Samaresh,Roy, Subhas Chandra
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p. 8597 - 8599
(2007/10/03)
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- A remarkable bismuth nitrate-catalyzed protection of carbonyl compounds
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Bismuth nitrate has been found to be an outstanding catalyst for the protection of carbonyl compounds as acetal, ketal, mixed ketal and thioketal with an excellent yield.
- Srivastava, Neeta,Dasgupta, Swapan K.,Banik, Bimal K.
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p. 1191 - 1193
(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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- 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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- Oxathioacetalization, thioacetalization and transthioacetalization of carbonyl compounds by N-bromosuccinimide: Selectivity and scope
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Efficient oxathioacetalization, thioacetalization and transthioacetalization of carbonyl compounds have been achieved in high yields employing N-bromosuccinimide as a catalyst.
- Kamal, Ahmed,Chouhan, Gagan,Ahmed, Kaleem
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p. 6947 - 6951
(2007/10/03)
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- Amberlyst 15 as a mild, chemoselective and reusable heterogeneous catalyst for the conversion of carbonyl compounds to 1,3-oxathiolanes
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The synthesis of 1,3-oxathiolanes from carbonyl compounds has been performed in good yields using Amberlyst15 as a convenient, reusable, heterogeneous catalyst. The procedure can be applied for the chemoselective protection of aldeydes in the presence of
- Ballini,Bosica,Maggi,Mazzacani,Righi,Sartori
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p. 1826 - 1829
(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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- SELECTIVE DESULFURIZATION OF 1,3-DITHIANES, -OXATHIOLANES AND -THIAZOLIDINES BY TRIBUTYLTIN HYDRIDE
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Selective desulfurization of 2-alkyl-1,3-dithianes, -oxathiolanes, or -thiazolidines 1 with one equivalent of tri-n-butyltin hydride yields acyclic compounds R1R2CHX(CH2)nSSnBu3 (X=S,O,NH; n=2,3), (2) which can be destannylated to the corresponding mercaptans 3.
- Schmidt, K.,O'Neal, S.,Chan, T.C.,Alexis, C.P.,Uribe, J.M.,et al.
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p. 7301 - 7304
(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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- 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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