- PhIO-Mediated oxidative dethioacetalization/dethioketalization under water-free conditions
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Treatment of thioacetals and thioketals with iodosobenzene in anhydrous DCM conveniently afforded the corresponding carbonyl compounds in high yields under water-free conditions. The mechanistic studies indicate that this dethioacetalization/dethioketalization process does not need water and the oxygen of the carbonyl products comes from the hypervalent iodine reagent.
- Du, Yunfei,Ouyang, Yaxin,Wang, Xi,Wang, Xiaofan,Yu, Zhenyang,Zhao, Bingyue,Zhao, Kang
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- 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
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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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- 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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- 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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- 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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- 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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- A mild method for the protection of aldehydes as dithioacetals and dithiolanes catalyzed by I2 generated in situ using Fe(NO 3)3.9H2O/Nai under heterogeneous conditions
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Structurally diverse aromatic aldehydes were thioacetalated in a clean and efficient reaction with ethane-1,2-dithiol and thiophenol based on the use of I2 generated in situ from Fe(NO3)3.9H 2O/NaI. The reaction occurs in good to high yield in dichloromethane at room temperature and the use of toxic and corrosive molecular iodine is avoided.
- Rostami, Amin,Nik, Heidar Ali Alavi,Roosta, Zahra Toodeh,Khazaei, Ardeshir
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experimental part
p. 431 - 434
(2009/12/03)
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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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- 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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- 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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- 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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- Chemoselective dithioacetalization of aldehydes using silica sulfuric acid as a reusable catalyst
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Silica sulfuric acid has been found to be an efficient and reusable catalyst for chemoselective dithioacetalization of aldehydes over ketones, in excellent yields.
- Pore,Desai, Uday V.,Mane,Wadgaonkar
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p. 1291 - 1295
(2007/10/03)
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- A simple and efficient heterogeneous procedure for thioacetalization of aldehydes and ketones
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A new procedure for the protection of aldehydes and ketones as thioacetals promoted by catalytic amount of p-toluene-sulfonic acid and silica gel has been developed. This procedure offers versatility, short reaction time, excellent yield, good selectivity
- Ali, Mohammed Hashmat,Gomes, Maria Goretti
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p. 1326 - 1332
(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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- Superoxide induced deprotection of 1,3-dithiolanes: A convenient method of dedithioacetalization
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Tetraethylammonium superoxide, generated in situ by the phase transfer reaction of potassium superoxide and tetra-ethylammonium bromide, brings about an easy deprotection of a variety of 1,3-dithiolanes of carbonyl compounds under significantly mild reaction conditions at room temperature.
- Shukla, Ajay Kumar,Verma, Manjusha,Singh, Krishna Nand
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p. 1748 - 1752
(2007/10/03)
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- ANHYDROUS LANTHANUM TRICHLORIDE, A MILD AND CONVENIENT REAGENT FOR THIOACETALIZATION
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Carbonyl compounds are thioacetalyzed easily by 1,2-ethanedithol in the presence of anhydrous LaCl3.
- Garlaschelli, Luigi,Vidari, Giovanni
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p. 5815 - 5816
(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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- 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 Formylation of an Aromatic Nucleus by the Use of 2-Ethoxy-1,3-dithiolane
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The reaction of various phenols with 2-ethoxy-1,3-dithiolane proceeded smoothly in the presence of BF3*Et2O to afford 1,3-dithiolan-2-ylated phenols, which were readily hydrolyzed to the corresponding aldehydes.This process was also extended to N,N-dimethylaniline and indole.
- Jo, Shigeo,Tanimoto, Shigeo,Sugimoto, Toyonari,Okano, Masaya
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p. 2120 - 2123
(2007/10/02)
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- The Reaction of 2-Ethoxy-1,3-dithiolane with Carbonyl Compounds
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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
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p. 1434 - 1436
(2007/10/02)
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