- Indium-Catalyzed Reductive Dithioacetalization of Carboxylic Acids with Dithiols: Scope, Limitations, and Application to Oxidative Desulfurization
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In this study an InI3-TMDS (1,1,3,3-tetramethyldisiloxane) reducing system effectively catalyzed the reductive dithioacetalization of a variety of aromatic and aliphatic carboxylic acids with 1,2-ethanedithiol or 1,3-propanedithiol leading to the one-pot preparation of either 1,3-dithiolane derivatives or a 1,3-dithiane derivative. Also, the intact indium catalyst continuously catalyzed the subsequent oxidative desulfurization of an in situ formed 1,3-dithiolane derivative, which led to the preparation of the corresponding aldehydes.
- Nishino, Kota,Minato, Kohei,Miyazaki, Takahiro,Ogiwara, Yohei,Sakai, Norio
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p. 3659 - 3665
(2017/04/11)
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- Phosphorylated Polyacrylonitrile Fibers as an Efficient and Greener Acetalization Catalyst
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A novel solid acid catalyst (PANEAPF) is developed by immobilization of phosphoric acid on polyacrylonitrile fiber through covalent bonding. Various characterization techniques such as elemental analysis (EA), X-ray photoelectron spectroscopy (XPS), Fourier transform infrared spectroscopy (FTIR), etc. are utilized to confirm the successful grafting and the stability of the fiber catalysts during application. PANEAPF shows high catalytic activity in the acetalization of aldehydes owing to the high utilization efficiency of its functionalized acid sites. In addition, the strong polarity micro-environment in the surface layers of PANEAPF make it highly suitable for catalytic application in both water and alcohol. Furthermore, the fiber catalyst can be applied to the acetalization of aldehydes in a continuous-flow process at room temperature, and shows excellent reactivity and superior recyclability (over 20 times). The many advantages of PANEAPF such as simple preparation, convenient regulation of acid amount, high durability, and eco-friendly process make it very attractive for fixed-bed reactors in the chemical industry.
- Xu, Gang,Cao, Jian,Zhao, Yali,Zheng, Lishuo,Tao, Minli,Zhang, Wenqin
-
supporting information
p. 2565 - 2575
(2017/09/25)
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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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- Sulfonated polyanthracene-catalyzed highly efficient and chemoselective thioacetalization of carbonyl compounds and transthioacetalization of acetals and acylals
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A straightforward and highly efficient procedure for the thioacetalization of a variety of aldehydes and transthioacetalization of acylals and acetals in good to excellent yields using catalytic amounts of sulfonated polyanthracene (S-PAT) is reported. Th
- Fahid,Pourmousavi
-
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- Efficient thioacetalisation of carbonyl compounds
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The thioacetalisation of a variety of heterocyclic, aromatic, and aliphatic carbonyl compounds (1 mmol) with ethane-1,2-dithiol (1 mmol) using silica sulphuric acid (SSA) is presented as an efficient heterogeneous catalyst under mild and solvent-free cond
- Habibi, Davood,Rahmani, Payam,Akbaripanah, Ziba
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p. 417 - 421
(2014/01/06)
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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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- Highly efficient and chemoselective method for the thioacetalization of aldehydes and transthioacetalization of acetals and acylals catalyzed by H 2SO4-silica under solvent-free conditions
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Chemoselective and efficient thioacetalization of a variety of aldehydes was achieved in excellent yields at room temperature using 1,2-ethanedithiol in the presence of catalytic amounts of H2SO4-silica. Thioacetals were also prepare
- Pourmousavi, Seied Ali,Kazemi, Shaghayegh Sadat
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experimental part
p. 917 - 923
(2012/07/16)
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- Oxidative cross-esterification of dithiolanes with alcohols through a cross-dehydrogenative coupling (CDC)/deprotection sequence
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An unprecedented oxidative cross-esterification in an equimolar mixture of dithiolanes, alcohols and water through a CDC/deprotection sequence has been developed. The reaction itself features simple experimental procedures under very mild conditions and offers a new strategic protocol for the direct and efficient synthesis of structurally diverse esters.
- Fu, Liang,Yao, Chang-Jiang,Chang, Ning-Jie,Chen, Jia-Rong,Lu, Liang-Qiu,Xiao, Wen-Jing
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supporting information; scheme or table
p. 506 - 508
(2012/01/15)
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- An efficient method for the transthioacetalization of acylals and acetals under mild conditions
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A rapid and efficient method for the transthioacetalization of acylals (1,1-diacetates) and acyclic and cyclic acetals is described. The reaction was carried out using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane tribromide (1 mol%). The yield of the transthioacetalization was high and reaction conditions involve the use of acetonitrile as the solvent at room temperature; isolation is simple and the products are nearly pure.
- Pourmousavi, Seied Ali,Hadavankhani, Majid,Zinati, Zahra
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experimental part
p. S495-S501
(2012/05/31)
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- Poly(N-bromobenzene-1,3-disulfonamide) and N,N,N′,N′- tetrabromobenzene-1,3-disulfonamide as a mild and efficient catalyst for chemoselective thioacetalization of carbonyl functions and transthioacetalization reactions
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Poly(N-bromobenzene-1,3-disulfonamide) and N,N,N′,N′- tetrabromobenzene-1,3-disulfonamide are effective catalysts for chemoselective dithioacetalization of aldehydes in the presence of ketones under neutral conditions.
- Veisi, Hojat,Ghorbani-Vaghei, Ramin,Dadamahaleh, Somayeh Akbari
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experimental part
p. 699 - 705
(2011/07/31)
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- Thioacetalization of aldehydes and ketones in SDS micelles
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Aromatic aldehydes have been successfully converted into their corresponding dithioacetal, dithiolane and dithiane derivatives in excellent yields with thiol (benzyl thiol and thiophenol), 1,2-ethanedithiol and 1,3-propanedithiol using trichloroacetic acid in sodium dodecyl sulfate micelles. The same procedure is applicable to ketones, but they need more time to be converted into their thioacetals. Image Presented.
- Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Tajik, Maryam,Soheilizad, Mehdi
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experimental part
p. 397 - 403
(2012/06/18)
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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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- 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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- Silica-PCl5: A novel heterogenous catalyst for simple and efficient chemoselective protection of carbonyl compounds
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A simple, efficient and environmentally benign procedure has been developed for chemoselective protection of carbonyl compounds using the newly developed heterogeneous catalyst: Silica-PCl5. A variety of aldehydes and ketones were efficiently c
- Pandey, Lokesh Kumar,Pathak, Uma,Tank, Rekha,Mazumder, Avik
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experimental part
p. 167 - 171
(2010/07/05)
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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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- A mild and chemoselective dithioacetalization of aldehydes in the presence of anhydrous copper (II) sulfate
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Various aldehydes have been protected with different thiols as dithioacetals with excellent yields using anhydrous copper sulfate as a mild and chemoselective catalyst. The reaction is carried out in a solvent and/or under solvent-free conditions. The transthioacetalization of oxyacetals into dithioacetals was also achieved in an excellent yield. Copyright Taylor & Francis Group, LLC.
- Moghaddam, Firouz Matloubi,Bardajee, Ghasem Rezanejade,Oskui, Afsane Arefi
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p. 1445 - 1450
(2007/10/03)
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- Chemoselective and solvent-free thioacetalization of aldehydes by a catalytic amount of NBS
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A chemoselective, straightforward, and rapid method for thioacetalization of aldehydes by use of 1,2-ethandithiol and a catalytic amount of N-bromosuccinimide under solvent-free conditions is reported. The reaction takes place in excellent yields and shor
- Hajipour, Abdol Reza,Ali Pourmousavi, Seied,Ruoho, Arnold E.
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p. 2807 - 2811
(2007/10/03)
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- A mild and chemoselective catalyst for thioacetalization under solvent free conditions
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Protection of a variety of carbonyl compounds as dithioacetals using P 2O5/SiO2 (75%), as a mild and chemoselective catalyst, was achieved under solvent free conditions in very good yields. Copyright Taylor & Francis Group
- Hajipour, Abdol R.,Zarei, Amin,Khazdooz, Leila,Zahmatkesh, Saeed,Ruoho, Arnold E.
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p. 387 - 395
(2007/10/03)
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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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- Ruthenium(III) chloride-catalyzed thioacetalization of carbonyl compounds: Scope, selectivity, and limitations
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A variety of carbonyl compounds can be easily and rapidly converted to the corresponding cyclic and acylic dithioacetals in the presence of a catalytic amount of ruthenium chloride in acetonitrile at room temperature. Some of the major advantages of this
- De, Surya Kanta
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p. 673 - 676
(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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- A facile and efficient procedure for the transdithioacetalization of 1,1-diacetates using POCl3-montmorillonite as catalyst
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A rapid and efficient method for the transdithioacetalization of 1,1-diacetates with 1,2-dithioglycol was described in good to excellent yield catalyzed by POCl3-montmorillonite.
- Jin, Tong-Shou,Sun, Guang,Li, Yan-Wei,Li, Tong-Shuang
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p. 4105 - 4110
(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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- Lutetium triflate as an efficient and recyclable catalyst for chemoselective thioacetalization of aldehydes
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Lutetium Inflate has been found to be an efficient and recyclable catalyst for chemoselective thioacetalization of aldehydes.
- De, Surya Kanta
-
p. 4401 - 4408
(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
-
p. 2837 - 2840
(2007/10/03)
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- Neodymium triflate as a recyclable catalyst for chemoselective thioacetalisation
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Neodymium triflate has been found to be an efficient and recyclable catalyst for the chemoselective protection of aldehydes.
- De, Surya Kanta
-
p. 230 - 231
(2007/10/03)
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- Chemoselective Protection of Carbonyl Compounds as Dithioacetals Using Silica Gel Supported Aluminium Chloride
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Silica gel supported aluminium chloride is shown to be a mild chemoselective catalyst for dithioacetalization of carbonyl compounds.
- Tamami,Borujeny, K. Parvanak
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p. 4253 - 4258
(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
-
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(III) chloride catalyzed efficient conversion of carbonyl compounds to 1,3-dithioacetals
-
Several aldehydes and ketones were efficiently converted into their corresponding dithioacetals and 1,3-dithianes in high yields using catalytic amount of indium(III) chloride in dichloromethane.
- Yadav,Subba Reddy,Pandey, Sushil Kumar
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p. 715 - 719
(2007/10/03)
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- A rapid and efficient method of thioacetalization of carbonyl compounds catalysed by POCl3-montmorillnite
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Aldehydes and ketones were thioactalized with 1,2-ethanedithiol in the presence POCl3-montmorillonite at room temperature in excellent yields.
- Jin,Sun,Ma,Li
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p. 1669 - 1673
(2007/10/03)
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- Trichloroisocyanuric acid as a mild and efficient catalyst for thioacetalization and transthio-acetalization reactions
-
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
-
p. 1641 - 1643
(2007/10/03)
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- Chemoselective dithioacetalisation of carbonyl compounds under solvent-free conditions
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Dithioacetalisation of carbonyl compounds in the presence of other structurally different aldehydes and ketones was achieved chemoselectively in the presence of Cdl2 under microwave irradiation in solvent free conditions.
- Laskar,Prajapati,Sandhu
-
p. 313 - 315
(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
-
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
-
-
- Zirconium tetrachloride (ZrCl4) catalyzed highly chemoselective and efficient transthioacetalization of acetals
-
Zirconium tetrachloride (ZrCl4) is an efficient catalyst for the highly chemoselective transthioacetalization of acetals under mild reaction conditions.
- Firouzabadi, Habib,Iranpoor, Nasser,Karimi, Babak
-
p. 319 - 320
(2007/10/03)
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- Tungsten hexachloride (WCl6) as an efficient catalyst for chemoselective dithioacetalization of carbonyl compounds and transthioacetalization of acetals
-
A variety of aldehydes, ketones and O,O-acetals were efficiently converted to the corresponding 1,3-dithianes and 1,3-dithiolanes by using catalytic amounts of tungsten hexachloride (WCl6) in CH2Cl2 under mild conditions.
- Firouzabadi, Habib,Iranpoor, Nasser,Karimi, Babak
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p. 739 - 740
(2007/10/03)
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- Envirocat EPZG(R) as an efficient heterogenous catalyst for thioacetalization of carbonyl compounds
-
The reaction of carbonyl compounds with 1,2-ethanedithiol was efficiently catalyzed by Envirocat EPZG(R) to afford the corresponding dithioacetals in excellent yields.
- Kasture,Bandgar,Sarkar,Wadgaonkar
-
p. 1579 - 1583
(2007/10/03)
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- Ahydrous Cobalt(II) Bromide Dispersed on Silica Gel: A Mild and Efficient Reagent for Thioacetalisation of Carbonyl Compounds
-
Anhydrous cobalt(II) bromide dispersed on silica gel has been shown to be a very efficient reagent system for thioacetalisation of a variety of aldehydes and ketones at room temperature.
- Patney, Harish K.
-
p. 5717 - 5718
(2007/10/02)
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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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- Chemoselective Protection of Aldehydes as Dithioacetals in Lithium Perchlorate-Diethyl Ether Medium. Evidence for the Formation of Oxocarbenium Ion Intermediate from Acetals
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Aldehydes and acetals were very efficiently converted to acyclic and cyclic dithioacetals in 5 M lithium perchlorate/diethyl ether (LPDE) medium at ambient temperature in high yields.Spectroscopic and other experimental evidences strongly suggest the formation of oxocarbenium ion intermediates from acetals in 5 M LPDE which subsequently reacted with thiols to give the dithioacetals.Under the same conditions ketones and their acetals also reacted, albeit very slowly compared to aldehydes and acetals, to yield dithioacetals.The difference in their reactivity was successfully employed in the chemoselective dithioacetalization of aldehydes and acetals in the presence of ketones and their acetals.The chemoselective dithioacetalization of keto aldehydes has been realized with the keto group remaining intact.The present method offers a convenient, efficient, and neutral medium for the deprotection of acetals to aldehydes and also the chemoselective protection of aldehydes to dithioacetals.
- Saraswathy, V. Geetha,Sankararaman, S.
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p. 4665 - 4670
(2007/10/02)
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- Bis(trimethylsilyl) sulfate-Silica Catalysed Thioacetalisation of Carbonyl Compounds
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Bis(trimethylsilyl)sulfate-silica has been shown to be an efficient reagent system for promoting thioacetalisation of carbonyl compounds at room temperature.
- Patney, Harish K.
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p. 7127 - 7128
(2007/10/02)
-
- Selective Protection of Carbonyl Compounds. Silica Gel Treated with Thionyl Chloride as an Effective Catalyst for Thioacetalization
-
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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- 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.
-
p. 235 - 243
(2007/10/02)
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- The Reaction of 2-Ethoxy-1,3-dithiolane with Carbonyl Compounds
-
The reaction of 2-ethoxy-1,3-dithiolane with carbonyl compounds such as aldehydes and ketones was investigated.The reaction proceeded smoothly in the presence of the HgCl2-catalyst to afford 2-substituted and 2,2-disubstituted 1,3-dithiolanes.The reaction
- Jo, Shigeo,Tanimoto, Shigeo,Oida, Tatsuo,Okano, Masaya
-
p. 1434 - 1436
(2007/10/02)
-