- Highly ordered mesoporous functionalized pyridinium protic ionic liquid framework as a highly efficient catalytic system in chemoselective thioacetalization of carbonyl compounds under solvent-free conditions
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Dithioacetals are a well-known class of organic compounds as both protecting group for the carbonyl compounds and valuable synthons for organic synthesis. Polysiloxane acidic ionic liquids containing pyridinium trifluoroacetate salts (PMO-Py-IL) as organi
- Karimi, Nafiseh,Luque, Rafael,Rajabi, Fatemeh,Voskressensky, Leonid
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- A 2 - substituted - 1, 3 - dithiane derivative of the preparation method
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The invention provides a preparation method of a 2-substituted-1,3-dithiane derivative. The preparation method comprises the following steps: adding 1,3-dithiane (CAS:505-23-7) and 1,2-dichloroethane (DCE) or dichloromethane (DCM) into a reaction bottle, adding N-chlorosuccinimide (NCS) under ice-bath condition, and stirring for 0.5-1 h to prepare a 2-chloro-1,3-dithiane solution; and adding an aldehyde or ketone compound and a lewis acid catalyst into the above solution, and reacting to prepare the 2-substituted-1,3-dithiane derivative. By using the 1,3-dithiane solid and different types of aldehyde and keto-carbonyl compounds as raw material and using one or more of ferric trichloride, boron trifluoride diethyl etherate, methanesulfonic acid, aluminum trichloride, ferrous chloride and nickel chloride as catalysts, preparation of the 2-substituted-1,3-dithiane derivative is realized. The catalysts used in the invention are cheap and easily available, dosage of the catalysts is low and pollution of the catalysts is little. The solid raw materials used in the invention can avoid use of fetid toxic 1,3-dimercaptopropane with strong volatility, and the purpose of protecting an experimenter's body and reducing environmental pollution is realized. In addition, the preparation method has advantages of mild reaction condition, high yield, simple operation and the like.
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Paragraph 0023; 0024; 0025; 0026; 0027; 0028
(2019/06/26)
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- Mesoporous sBa-15 silica catalyst functionalized with phenylsulfonic acid groups (SbA-15-ph-So3h) as efficient nanocatalyst for chemoselective thioacetalization of carbonyl compounds
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In this research a Nano acidic catalyst was prepared and its efficiency on thioacetalization of carbonyl compounds was examined. For this aim we used modified SBA-15 as support, which have been modified by phenolic and sulfonic acid. SBA-15 is a member of
- Sedrpoushan, Alireza,Ghazizadeh, Habibollah
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p. 112 - 118
(2017/01/18)
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- Stereoselective synthesis of allyl ethers using α,β-unsaturated acylsilanes
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The reaction behavior of silylvinylmethanols with acid catalysts was investigated. The starting silylvinylmethanols 2 were prepared by the reaction of the corresponding α,β-unsaturated acylsilanes 1 with organocerium reagents. The reaction of 2 with TsOH
- Honda, Mitsunori,Takatera, Takehide,Ui, Ryosuke,Kunimoto, Ko-Ki,Segi, Masahito
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p. 864 - 869
(2017/02/18)
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- SBA-15 functionalized sulfonic acid containing a confined hydrophobic and acidic ionic liquid: A highly efficient catalyst for solvent-free thioacetalization of carbonyl compounds at room temperature
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A novel application of SBA-15 functionalized sulfonic acid containing a confined ionic liquid has been introduced to convert various carbonyl compounds to their corresponding dithioacetals and dithioketals at room temperature and under solvent-free condit
- Karimi, Babak,Vafaeezadeh, Majid
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p. 23207 - 23211
(2013/11/19)
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- Aluminum hydrogen sulfate [Al(HSO4)3] as an efficient catalyst for the preparation of thioacetals
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Aluminum hydrogen sulfate, as a heterogeneous solid acid catalyst, has been used for the mild conversion of carbonyl compounds to their thioacetals using 1,2- and 1,3-dithiol under ambient conditions with short reaction times in high to excellent yield in
- Ghashang, Majid
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p. 2837 - 2842
(2013/07/26)
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- Silica phenyl sulfonic acid as a solid acid heterogeneous catalyst for chemoselective thioacetalization of carbonyl compounds and dethioacetalization under mild conditions
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Silica phenyl sulfonic acid (SPSA) is an effective catalyst for chemoselective thioacetalization of aldehydes in the presence of ketones under neutral conditions. In addition, a simple and an efficient procedure for deprotection of 1,3-dithianes and 1,3-dithiolanes of aromatic, aliphatic, and α,β-unsaturated aldehydes and ketones in the solvent-free to the corresponding parent carbonyl compounds was successfully carried out with SPSA in excellent yields.
- Veisi, Hojat,Sedrpoushan, Alireza,Zolfigol, Mohammad Ali,Mohanazadeh, Farajollah,Hemmati, Saba
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p. E204-E206
(2013/06/04)
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- Chemoselective and odorless transthioacetalization of acetals using α-oxo-ketene dithioacetals as thiol equivalents
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Using α-oxo-ketene dithioacetals 1a as odorless thiol equivlents, an efficient and odorless transthioacetalization of acetals 2 has been developed. In the presence of MeCOCl in MeOH, the cleavage of 1a commences to generate thiols at both room and reflux temperatures, and the generated thiols then react with acetals 2 to give correspecting thioacetals 3 in good yield. This transthioacetalization is characterized by mild reaction conditions, simple procedure, good yields, and perfect chemoselectivity. It is noteworthy that only a very faint odor of thiols can be perceived during both the reaction and workup.
- Yu, Hai-Feng
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p. 1280 - 1286
(2013/04/10)
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- Synthesis of 1,3-dithiane and 1,3-dithiolane derivatives by tungstate sulfuric acid: Recyclable and green catalyst
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An efficient, novel, and environmentally benign procedure for the thioacetalization of aliphatic and aromatic carbonyl compounds in the presence of catalytic amounts of tungstate sulfuric acid under solvent-free conditions to afford 1,3-dithianes and 1,3-
- Karami, Bahador,Taei, Mahbubeh,Khodabakhshi, Saeed,Jamshidi, Masih
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experimental part
p. 65 - 74
(2012/07/14)
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- Dithioacetalization of carbonyl compounds under catalyst-free condition
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Protection of carbonyl compounds with 1,3-propanedithiol under a catalyst-free condition in nitromethane as a solvent has been described.
- Akhlaghinia, Batool,Makarem, Ata
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scheme or table
p. 575 - 581
(2012/04/23)
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- Silica-supported phosphorus pentoxide: A reusable catalyst for S,S-acetalization of carbonyl groups under ambient conditions
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Phosphorus pentoxide supported on silica gel (P2O 5/SiO2) efficiently acts as a highly active and reusable catalyst for cyclic and non-cyclic S,S-acetalization of a variety of carbonyl compounds under mild, solvent-free an
- Shaterian, Hamid Reza,Azizi, Kobra,Fahimi, Nafiseh
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experimental part
p. 85 - 91
(2012/01/06)
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- Preyssler-type heteropoly acid: A new, mild and efficient catalyst for protection of carbonyl compounds
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Preyssler-type heteropoly acid is introduced as a new, mild and efficient catalyst for protection of a variety of carbonyl compounds with 1,3-propane dithiol.
- Rahimizadeh, Mohammad,Bazazan, Tahmineh,Shiri, Ali,Bakavoli, Mehdi,Hassani, Hassan
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experimental part
p. 435 - 438
(2012/01/03)
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- Chemoselective (trans)thioacetalization of carbonyl compounds with a reusable lewis acid-surfactant-combined copper bis(dodecyl sulfate) catalyst in water
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A Lewis acid-surfactant-combined copper bis(dodecyl sulfate) [Cu(DS) 2] catalyst served as an efficient and reusable catalyst for the thioacetalization and transthioacetalization of carbonyl compounds and O,O-acetals in water at room temperature. Some of the major advantages of this procedure are high chemoselectivity, ease of operation and purification without any organic solvent, and high yields. Georg Thieme Verlag Stuttgart.
- Weng, Shiue-Shien,Chang, Shen-Chun,Chang, Tsuan-Hao,Chyn, Jong-Pyng,Lee, Shu-Wei,Lin, Chao-An,Chen, Fong-Kuang
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experimental part
p. 1493 - 1499
(2010/10/03)
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- 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a mild and efficient catalyst for chemoselective thioacetalization of carbonyl compounds and dethioacetalization under mild conditions
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Hydantoin bromide is an effective catalyst for chemoselective thioacetalization of aldehydes in the presence of ketones under neutral conditions. In addition, a simple and efficient procedure for the deprotection of 1,3-dithianes and 1,3-dithiolanes of ar
- Veisi, Hojat,Amiri, Mostafa,Hamidian, Amir Hossein,Malakootikhah, Javad,Fatolahi, Leila,Faraji, Alireza,Sedrpoushan, Alireza,Maleki, Behrooz,Saremi, Shokufe Ghahri,Noroozi, Mohammad,Bahadoori, Fatemeh,Veisi, Somayeh
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experimental part
p. 689 - 696
(2010/06/19)
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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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- Efficient method for thioacetalization of carbonyl compounds in the presence of a catalytic amount of benzyltriphenylphosphonium tribromide (BTPTB) under solvent-free conditions
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A variety of carbonyl compounds have been successfully converted to the corresponding thioacetal derivatives in good to excellent yields on reaction of carbonyl compounds with 1,2-ethanedithiole, 1,3-propanedithiol, and ethylthiol in the presence of a cat
- Hajipour, Abdol Reza,Pourmousavi, Seied A.,Ruoho, Arnold E.
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p. 2548 - 2566
(2008/12/22)
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- Ferric hydrogensulfate as effective and recyclable catalyst for mild dithioacetalization of aldehydes and ketones
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Ferric hydrogensulfate has been found to be an extremely efficient and recyclable heterogeneous catalyst for dithioacetalization reactions. Carbonyl compounds have been successfully converted into their corresponding dithiolanes and dithianes derivatives
- Shaterian, Hamid Reza,Ahmadian, Hamid Reza,Ghashang, Majid,Doostmohammadi, Razieh,Yarahmadi, Hossein
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experimental part
p. 1099 - 1108
(2009/04/07)
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- Chemoselective dithioacetalization of carbonyl compounds using magnesium hydrogensulfate as efficient heterogeneous catalyst
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Carbonyl compounds have been successfully converted into their corresponding dithiolanes and dithianes derivatives with 1,2-ethanedithiol and 1,3-propanedithiol in excellent yield at room temperature and short reaction times using a catalytic amount of ma
- Shaterian, Hamid Reza,Hosseinian, Asghar,Ghashang, Majid,Khorami, Fahimeh
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experimental part
p. 2490 - 2501
(2009/08/07)
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- Acid-promoted thioacetalization in water using 2-(1,3-dithian-2-ylidene) malonic acid as an odorless and efficient thioacetalization reagent
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Thioacetalization using 2-(1,3-dithian-2-ylidene)malonic acid 1 as a nonthiolic, odorless 1,3-propanedithiol equivalent promoted by p-dodecylbenzenesulfonic acid in water has been achieved. A range of selected carbonyl compounds 2 was converted into the corresponding dithioacetals 3 in high yields. Moreover, the thioacetalization showed high chemoselectivity between aldehydes and ketones. Copyright Taylor & Francis Group, LLC.
- Ouyang, Yan,Dong, Dewen,Liang, Yongjiu,Chai, Yanyan,Liu, Qun
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p. 993 - 1000
(2007/10/03)
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- An efficient method for thioacetalization of carbonyl compounds in the presence of a catalytic amount of benzyltriphenylphosphonium tribromide under solvent-free conditions
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A variety of carbonyl compounds have been successfully converted to the corresponding thioacetal derivatives in good to excellent yields on the reaction of carbonyl compounds with 1,2-ethanedithiole, 1,3-propanedithiol, and ethanethiol in the presence of
- Hajipour, Abdol R.,Pourmousavi, Seied A.,Ruoho, Arnold E.
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p. 921 - 937
(2008/02/05)
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- Bismuth oxide perchlorate as a highly efficient and chemoselective catalyst for thioacetalization of carbonyl compounds under solvent-free conditions
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Bismuth oxide perchlorate efficiently and chemoselectively catalyzes the thioacetalization of both aliphatic and aromatic carbonyl compounds under solvent-free conditions. Stearically hindered ketones are also thioacetalized in excellent yields with stoic
- Sunil Kumar,Thirupathi Reddy,Narsimha Reddy,Rao,Rajitha
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p. 2387 - 2389
(2007/10/03)
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- Chemoselective thioacetalization with odorless 2-(1,3-dithian-2-ylidene)-3- oxobutanoic acid as a 1,3-propanedithiol equivalent
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Odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid (1c) was prepared and investigated in the thioacetalization of carbonyl compounds as a 1,3-propanedithiol equivalent. The results showed that the thioacetalization of various carbonyl compounds 2 with 1c proceeded smoothly and afforded the corresponding dithioacetals 3 in high yields (up to 99%) in the presence of acetyl chloride at room or reflux temperatures. Moreover, the thioacetalization exhibited high chemoselectivity between aldehydes and ketones.
- Yu, Haifeng,Dong, Dewen,Ouyang, Yan,Liu, Qun
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p. 1741 - 1745
(2007/10/03)
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- Chemoselective thioacetalisation and transthioacetalisation of carbonyl compounds catalysed by tetrabutylammonium tribromide (TBATB)
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Thioacetals and thioketals of various aldehydes and ketones were obtained directly from carbonyl compounds or by a transthioacetalisation process from cyclic O,O-acetals in the presence of dithiols and a catalytic amount of tetrabutylammonium tribromide (TBATB). Chemoselective thioacetalisation of aromatic aldehydes containing an electron-donating group in the presence of an aldehyde containing an electron-withdrawing group, aldehydes in the presence of ketones, aliphatic cyclic ketones in the presence of aromatic ketones and less hindered ketones in the presence of more hindered ketones have been achieved. A cyclic acetal containing an electron-donating group has been chemoselectively transthioacetalised in the presence of an acetal having an electron-withdrawing substituent. These selectivities are due to the intrinsic reactivity of the substrate themselves and are independent of the catalyst and reaction conditions, Shorter reaction times, mild reaction conditions, stability of acid sensitive protecting groups, high efficiencies, facile isolation of the desired products and the catalytic nature of the reagent are the attractive features of the present method.
- Naik, Sarala,Gopinath, Rangam,Goswami, Mousumi,Patel, Bhisma K.
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p. 1670 - 1677
(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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- Cobalt(II)chloride catalyzed chemoselective thioacetalization of aldehydes
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A mild and chemoselective dithioacetalization procedure for the protection of various aldehydes in the presence of catalytic amount of cobalt(II)chloride is described.
- De, Surya Kanta
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p. 1035 - 1036
(2007/10/03)
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- α,α-diacetyl cyclic ketene dithioacetals: Odorless and efficient dithiol equivalents in thioacetalization reactions
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Two novel, non-thiolic, odorless dithiol equivalents, α,α- diacetyl cyclic ketene dithioacetals 2a and 2b, had been developed. A range of carbonyl compounds 3 were converted into corresponding dithioacetals, dithianes 4 and dithiolanes 5, in high yields (up to 99%) in the presence of 2a or 2b. Moreover, 2a and 2b show high chemoselectivity between aldehyde and ketone in thioacetalization.
- Yu, Haifeng,Liu, Qun,Yin, Yanbing,Fang, Qunxin,Zhang, Jingping,Dong, Dewen
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p. 999 - 1002
(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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- Heteropoly acids as heterogeneous catalysts for thioacetalization and transthioacetalization reactions
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Heteropoly acids are effective solid catalysts for the thioacetalization of carbonyl compounds. Tungstophosphoric acid (H3PW12O40), was found to be an effective and a highly selective catalyst for the thioacetalization of aldehydes, ketones and for the transthioacetalization of acetals, acylals and O,S-acetals which proceeded in excellent yields in the absence of solvent. The catalyst has also been successfully applied to the chemoselective conversion of α- or β-diketones and a β-keto ester into the corresponding dithioacetals. Sterically hindered carbonyl compounds such as camphor and benzophenone were also converted to their corresponding thioacetals in refluxing petroleum ether in 89-94percent yields. Surprisingly, anthrone was reduced to anthracene in 91percent yield.
- Firouzabadi,Iranpoor,Amani
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- Neutral lithium triflate (LiOTf) efficiently catalyzes chemoselective preparations of cyclic and acyclic dithioacetals from carbonyl compounds, acylals, and O,O-cyclic and open-chain acetals under solvent-free conditions
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An efficient and chemoselective preparation of cyclic and acyclic thioacetals from carbonyl compounds, cyclic and acyclic acetals and acylals in the presence of catalytic amounts of neutral lithium triflate and thiols under solvent-free conditions is described.
- Firouzabadi, Habib,Eslami, Shahram,Karimi, Babak
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p. 2401 - 2406
(2007/10/03)
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- Molybdenum pentachloride (MoCl5) catalyzes efficient dithioacetalization of carbonyl compounds and transdithioacetalization of O, O-acetals. This catalyst also conducts efficient non-hydrolytic deprotection of dithioacetals in the presence of dry DMSO. Part 2
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Dithioacetalization of carbonyl compounds was performed efficiently in CH2Cl2 at room temperature in the presence of MoCl5. Highly selective transdithioacetalization of acetals was also catalyzed efficiently by this catalyst. MoCl5 performed non-hydrolytic deprotection of dithioacetals in the presence of dry DMSO.
- Firouzabadi,Karimi
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p. 207 - 216
(2007/10/03)
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- Trichloroisocyanuric acid as a mild and efficient catalyst for thioacetalization and transthio-acetalization reactions
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Trichloroisocyanuric acid (1), a cheap industrial chemical, catalyzes mild and efficient thioacetalization and transthioacetalization reactions. In addition, this catalyst is very selective for this purpose.
- Firouzabadi,Iranpoor,Hazarkhani
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p. 1641 - 1643
(2007/10/03)
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- Lithium trifluoromethanesulfonate (LiOTf) as a highly efficient catalyst for chemoselective dithioacetalization of carbonyl compounds under neutral and solvent-free conditions
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Various types of carbonyl compound can be efficiently and chemoselectively converted to their corresponding dithioacetals in the presence of catalytic amounts of lithium triflate under solvent-free conditions. Due to the neutrality of the reaction medium, this method is especially useful for acid sensitive substrates.
- Firouzabadi, Habib,Karimi, Babak,Eslami, Shahram
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p. 4055 - 4058
(2007/10/03)
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- Lithium bromide-catalyzed highly chemoselective and efficient dithioacetalization of α,β-unsaturated and aromatic aldehydes under solvent-free conditions
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Chemoselective dithioacetalization of aromatic- and α,β- unsaturated aldehydes in the presence of other structurally different aldehydes and ketones was achieved efficiently in the presence of catalytic amounts of LiBr under solvent-free conditions. Due to the neutral reaction conditions, this method is compatible with acid sensitive substrates.
- Firouzabadi, Habib,Iranpoor, Nasser,Karimi, Babak
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- Pyrylium Salt Sensitized Photochemical Deprotections of Dithioacetals and Ketals
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Photoreactions of various dithioacetals and ketals using tris(p-chlorophenyl)pyrylium perchlorate as a sensitizer were studied.Irradiation (λ>360 nm) of dichloromethane solutions containing dithioacetals or ketals and pyrylium salt afforded the corresponding carbonyl compounds in good to excellent yields in the presence of molecular oxygen.
- Kamata, Masaki,Murakami, Yukiko,Tamagawa, Yasuko,Kato, Mitsuaki,Hasegawa, Eietsu
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p. 12821 - 12828
(2007/10/02)
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- Tellurium tetrachloride as a mild and efficient catalyst for dithioacetalization
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A variety of aldehydes and aliphatic ketones were converted into the corresponding dithioacetals at room temperature in good yields by using small amounts of tellurium tetrachloride as a mild Lewis acid catalyst.
- Tani, Hiroyuki,Masumoto, Kazunori,Inamasu, Tokuo,Suzuki, Hitomi
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p. 2039 - 2042
(2007/10/02)
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- Selective Protection of Carbonyl Compounds. Silica Gel Treated with Thionyl Chloride as an Effective Catalyst for Thioacetalization
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Silica gel treated with thionyl chloride was found to be an effective as well as highly selective catalyst for thioacetalization of aldehydes.With the use of this catalyst 1,3-dithioranes and 1,3-dithianes were obtained in excellent yields from various aldehydes.Under the same conditions ketones were similarly but more slowly thioketalized.This difference in reactivity between aldehydes and ketones was successfully utilized for the thioacetalization of aldehydes in the presence of ketones and also for the chemoselective conversion of keto aldehydes into the corresponding dithioacetals with the keto group remaining intact.
- Kamitori, Yasuhiro,Hojo, Masaru,Masuda, Ryoichi,Kimura, Tadashi,Yoshida, Tatsushi
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p. 1427 - 1431
(2007/10/02)
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- Lithium keten thioacetalides. Factors influencing α- versus γ-alkylation
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Alkylation of the lithium salt of the vinyl-1,3-dithian (2; R = CH 3) occurred exclusively at the α-carbon. However both α- and γ-alkylation was observed with the substrate (2; R = C 6H5). A systematic investigation reveal
- Murphy, William S.,Wattanasin, Sompong
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p. 2678 - 2682
(2007/10/02)
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