- 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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- Highly efficient and chemoselective thioacetalization of carbonyl compounds catalyzed with aluminum trifluromethanesulfonate [Al(OTf)3]
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Aluminum trifluromethanesulfonate [Al(OTf)3] is a highly efficient and chemoselective catalyst for the thioacetalization of carbonyl compounds.
- Firouzabadi,Iranpoor,Kohmareh
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- Highly efficient transdithioacetalization of acetals catalyzed by silica chloride
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A modified procedure for the preparation of a silica chloride with higher chloride capacity than that reported is described. Moreover, this silica chloride was found to be an effective catalyst for chemoselective and highly efficient transdithioacetalization of different classes of acetals.
- Firouzabadi, Habib,Iranpoor, Nasser,Karimi, Babak,Hazarkhani, Hassan
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- Mesoporous silica-functionalized dual Br?nsted acidic ionic liquid as an efficient catalyst for thioacetalization of carbonyl compounds in water
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A novel silica-functionalized dual Br?nsted acidic ionic liquid (ionic liquid with two Br?nsted acidic species) has been reported as a highly efficient catalyst for thioacetalization of carbonyl compounds. The reaction was efficiently performed in water a
- Vafaeezadeh, Majid,Dizicheh, Zahra Bahrami,Hashemi, Mohammad Mahmoodi
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- Polymer-assisted dithane hydrolysis with minimum workup
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(Chemical Equation Presented) The first solid-phase-assisted protocol for the hydrolysis of dithioacetals is described using three different functionalized ion exchange resins. The hydrolysis and the purification proceed under milder conditions than common homogeneously employed reagents so that very reactive carbonyl compounds can be prepared.
- Luiken, Silke,Kirschning, Andreas
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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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- 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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- 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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- The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization
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2-[2-Chloro-1-(1-chlorovinyl)allylidene]-1,3-dithiane 1 was synthesized by the chlorination of 3-(1,3)-dithianylidenepentane-2,4-dione 2 using the Vilsmeier-Haack reagent in 99% yield. As a novel nonthiolic, odorless 1,3-propane-dithiol equivalent, 1 was investigated in the thioacetalization reaction. Various types of aldehydes and ketones 3 were converted to the corresponding dithianes 4 in the presence of 1 in high yields (79-97%). Moreover, 1 exhibited obvious chemoselectivity between aldehyde and ketone in this thioacetalization reaction. A mechanism for this thioacetalization reaction is proposed.
- Liu, Qun,Che, Guangbo,Yu, Haifeng,Liu, Yingchun,Zhang, Jingping,Zhang, Qian,Dong, Dewen
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- Silica-supported perchloric acid (HClO4-SiO2): A versatile catalyst for tetrahydropyranylation, oxathioacetalization and thioacetalization
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A simple and convenient synthetic protocol for the protection of hydroxyl group as tetrahydropyranyl ether as well as carbonyl functionality as oxathioacetal and thioacetal has been achieved using a catalytic amount of silica-supported perchloric acid und
- Khan, Abu T.,Parvin, Tasneem,Choudhury, Lokman H.
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- An expeditious synthesis of dithioacetals using zeolites
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A simple and efficient catalytic method for dithioacetalization of various carbonyl compounds (saturated and α,β-unsaturated aliphatic, aromatic, heteroaromatic and hindered) with ethanethiol and 1,3-propanedithiol using H-Y and H-mordenite (H-M) zeolites
- Kumar,Reddy,Singh,Pandey
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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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- 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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- Super electron donor-mediated reductive desulfurization reactions
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The desulfurization of thioacetals and thioethers by a pyridine-derived electron donor is described. This methodology provides efficient access to the reduced products in high yields and does not require the use of transition-metals, elemental alkali-metals, or hydrogen atom donors.
- Nozawa-Kumada, Kanako,Ito, Shungo,Noguchi, Koto,Shigeno, Masanori,Kondo, Yoshinori
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supporting information
p. 12968 - 12971
(2019/11/05)
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- Chlorotrimethylsilane and Sodium Iodide: A Remarkable Metal-Free Association for the Desulfurization of Benzylic Dithioketals under Mild Conditions
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A novel metal-free process allowing the reductive desulfurization of various benzylic dithioketals to afford diarylmethane and benzylester derivatives with good to excellent yields is reported. At room temperature, this mild reduction process requires only the use of TMSCl and NaI in CH2Cl2 and tolerates a large variety of functional groups. (Figure presented.).
- Zhao, Guangkuan,Yuan, Ling-Zhi,Alami, Mouad,Provot, Olivier
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p. 2522 - 2536
(2018/05/14)
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- KOtBu: A Privileged Reagent for Electron Transfer Reactions?
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Many recent studies have used KOtBu in organic reactions that involve single electron transfer; in the literature, the electron transfer is proposed to occur either directly from the metal alkoxide or indirectly, following reaction of the alkoxide with a solvent or additive. These reaction classes include coupling reactions of halobenzenes and arenes, reductive cleavages of dithianes, and SRN1 reactions. Direct electron transfer would imply that alkali metal alkoxides are willing partners in these electron transfer reactions, but the literature reports provide little or no experimental evidence for this. This paper examines each of these classes of reaction in turn, and contests the roles proposed for KOtBu; instead, it provides new mechanistic information that in each case supports the in situ formation of organic electron donors. We go on to show that direct electron transfer from KOtBu can however occur in appropriate cases, where the electron acceptor has a reduction potential near the oxidation potential of KOtBu, and the example that we use is CBr4. In this case, computational results support electrochemical data in backing a direct electron transfer reaction.
- Barham, Joshua P.,Coulthard, Graeme,Emery, Katie J.,Doni, Eswararao,Cumine, Florimond,Nocera, Giuseppe,John, Matthew P.,Berlouis, Leonard E. A.,McGuire, Thomas,Tuttle, Tell,Murphy, John A.
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supporting information
p. 7402 - 7410
(2016/07/06)
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- Palladium-catalyzed cross-coupling of 2-aryl-1,3-dithianes
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Palladium-catalyzed cross-coupling of aryl bromides with 2-aryl-1,3-dithianes is described. This methodology takes advantage of the relatively acidic benzylic proton of the dithiane, allowing it to act as a competent, polarity-reversed transmetalation reagent. This unique approach affords the ability to employ an orthogonal deprotection strategy, and practical routes to both diaryl ketones and diarylmethanes are illustrated. Cross-coupling of a range of aryl dithianes with aryl bromides, including scope and current limitations, is presented.
- Dockrey, Summer A. Baker,Makepeace, Alicia K.,Schmink, Jason R.
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p. 4730 - 4733
(2015/04/27)
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- Reversed-polarity synthesis of diaryl ketones through palladium-catalyzed direct arylation of 2-Aryl-1,3-dithianes
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An umpolung approach to the synthesis of diaryl ketones has been developed based on in situ generation of acyl anion equivalents and their catalytic arylation. This method entails the base-promoted, palladium-catalyzed direct C-H arylation of 2- aryl-1,3-dithianes with aryl bromides. Use of ( SiMe3)2 (M=Li, Na) base results in reversible deprotonation of the weakly acidic dithiane. In the presence of a Pd(NiXantphos)-based catalyst and aryl bromide, cross-coupling of the metallated 2-aryl- 1,3-dithiane takes place under mild conditions (2 h at rt) with yields as high as 96%. The resulting 2,2- diaryl-1,3-dithianes were converted into diaryl ketones by either molecular iodine, N-bromo succinimide (NBS) or Selectfluor in the presence of water. The dithiane arylation/hydrolysis can be performed in a one-pot procedure to yield a variety of diaryl ketones in good to excellent yields. This method is suitable for rapid and large-scale synthesis of diaryl ketones. A one-pot preparation of anti-cholesterol drug fenofibrate (TriCor) has been achieved on 10.0 mmol scale in 86% yield.
- Yucel, Baris,Walsh, Patrick J.
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p. 3659 - 3667
(2015/01/09)
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- Reversed-polarity synthesis of Diaryl Ketones through palladium-catalyzed direct Arylation of 2-Aryl-1,3-dithianes
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An umpolung approach to the synthesis of diaryl ketones has been developed based on in situ generation of acyl anion equivalents and their catalytic arylation. This method entails the base-promoted, palladium-catalyzed direct C-H arylation of 2- aryl-1,3-dithianes with aryl bromides. Use of MNACHTUNGTRENUNG( SiMe3)2 (M=Li, Na) base results in reversible deprotonation of the weakly acidic dithiane. In the presence of a Pd(NiXantphos)-based catalyst and aryl bromide, cross-coupling of the metallated 2-aryl- 1,3-dithiane takes place under mild conditions (2 h at rt) with yields as high as 96%. The resulting 2,2- diaryl-1,3-dithianes were converted into diaryl ketones by either molecular iodine, N-bromo succinimide (NBS) or Selectfluor in the presence of water. The dithiane arylation/hydrolysis can be performed in a one-pot procedure to yield a variety of diaryl ketones in good to excellent yields. This method is suitable for rapid and large-scale synthesis of diaryl ketones. A one-pot preparation of anti-cholesterol drug fenofibrate (TriCor) has been achieved on 10.0 mmol scale in 86% yield.
- Yucel, Baris,Walsh, Patrick J.
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supporting information
p. 3659 - 3667
(2015/01/09)
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- Studies on the double alkylation of 2,2-disubstituted-1,3- dithiacycloalkane-S-oxides: Synthesis of tertiary thiol derivatives
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Di-alkylation of 2,2-dimethyl-1,3-dithiacycloalkane-S-oxides has been achieved allowing the synthesis of two tertiary thiol centres. The diastereoisomers of the mono-alkylated products have been shown to react at different rates. The X-ray crystal structures of three substituted dithiane-S-oxides have been determined, and the conversion of the dialkylated products into cyclic disulfide derivatives of tertiary thiols (1,2-dithiolanes) has been achieved by treatment with acid. The Royal Society of Chemistry 2013.
- Fuchs, Christian,Edgar, Mark,Elsegood, Mark R. J.,Weaver, George W.
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p. 21911 - 21918
(2013/11/06)
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- Facile deprotection of dithioacetals by using a novel 1,4-benzoquinone/cat. NaI system
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The combination of 1,4-benzoquinone and a catalytic amount of NaI was found to be effective for the deprotection of dithioacetals. The reactions proceeded efficiently under mild, near-neutral reaction conditions, producing a wide range of aryl and alkyl aldehydes and ketones generally in high yields with good functional group compatibility. The method developed therefore represents a general, facile, and highly applicable approach for deprotecting dithioacetals.
- Inamoto, Kiyofumi,Yamada, Tetsuya,Kato, Sei-Ichi,Kikkawa, Shoko,Kondo, Yoshinori
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p. 9192 - 9199
(2013/10/01)
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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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- Synthesis and deprotection of 1,3-Dithianes and 1,3-Dithiolanes by polyphosphoric acid
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A simply, mild and efficient method for the deprotection of 1,3-dithianes and 1,3-dithiolanes to their corresponding carbonyl compounds using a mixture of polyphosphoric acid and acetic acid at 20-45 °C is reported.
- Jin, Yong-Sheng,Zhang, Wei,Zhang, Da-Zhi,Qiao, Li-Ming,Wu, Qiu-Ye,Chen, Hai-Sheng
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scheme or table
p. 1117 - 1119
(2011/12/16)
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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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- 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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- Cleavage of 1,3-dithianes via acid-catalyzed hydrolysis of the corresponding 1,3-dithianemonooxides
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The hydrolysis of 1,3-dithianes to their parent carbonyl compounds via their corresponding monosulfoxides was systematically investigated. The oxidation of the 1,3-dithianes was carried out in high yields using tert-butyl hydroperoxide. Acid-catalyzed hydrolysis of the monosulfoxides to the carbonyl compounds was then performed in excellent yields. The cleavage reactions were monitored by gas chromatography and kinetics were investigated on substrates varying in electron density and steric requirements. Neither effect prevented high overall yields in the cleavage reaction. Georg Thieme Verlag Stuttgart.
- Krohn, Karsten,Cludius-Brandt, Stephan
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body text
p. 2369 - 2372
(2009/04/07)
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- An efficient, continuous flow technique for the chemoselective synthesis of thioacetals
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By optimizing a reagent's residence time within a packed-bed reactor, it is possible to overcome selectivity issues frequently encountered in stirred reaction vessels. This important feature is demonstrated for the chemoselective protection of 4-acetylben
- Wiles, Charlotte,Watts, Paul,Haswell, Stephen J.
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p. 7362 - 7365
(2008/03/13)
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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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- A simple and practical synthetic protocol for thioacetalization of carbonyl compounds
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Various aldehydes and ketones are smoothly converted to the corresponding acyclic and cyclic dithioacetals in very good yields by employing catalytic amount of acetyl chloride at room temperature under solvent-free conditions. Some of the major advantages of this procedure are its mild reaction conditions, highly efficient and selective, good yields, economically cheaper and compatible in the presence of a wide variety of other protecting groups.
- Khan, Abu T.,Mondal, Ejabul
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p. 844 - 850
(2007/10/03)
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- Odorless thioacetalization reagent 2-[1,3] dithian-2-ylidene-3-oxo- butanamide and its chemoselectivity
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2-[1,3]Dithian/dithiolan-2-ylidene-3-oxo-butanamide 2a/2b were synthesized and investigated in the thioacetalization reaction of aldehydes/ketones 3. The experiments revealed that 2a could be used as a nonthiolic, odorless 1,3-propanedithiol equivalent in the conversion of aldehydes/ketones into the corresponding dithianes 4, however, 2b was less effective. Moreover, the chemoselectivity of the thioacetalization of 3 in the presence of 2a is discussed.
- Liu, Jun,Liu, Qun,Yu, Haifeng,Ouyang, Yan,Dong, Dewen
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p. 4545 - 4556
(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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- Oxidative deprotection of 1,3-dithiane group using NaClO2 and NaH2PO4 in aqueous methanol
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The 1,3-dithiane group was oxidatively deprotected under the conditions of sodium chlorite, sodium dihydrogenphosphate, and 2-methyl-2-butene in 3:1 methanol-water at room temperature in good yield.
- Ichige, Takahiro,Miyake, Annu,Kanoh, Naoki,Nakata, Masaya
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p. 1686 - 1690
(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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- A general alternative to obtain S.S-acetals using taff, a bentonitic clay, as the catalyst
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A one-pot general alternative to prepare dithioacetals, with excellent yields, via the condensation of 1,3-propanedithiol, benzyl, and n-butyl mercapthanes with several carbonylic compounds using a bentonitic earth as the catalyst is proposed. Also, the a
- Miranda,Osnaya,Garduno,Delgado,Alvarez,Salmon
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p. 1587 - 1597
(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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- A silver salt - iodine reagent system for the deprotection of monothioacetals and dithioacetals
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A new reagent (silver salt - iodine) system was developed for the deprotection of monothioacetals and dithioacetals. The reactions using this reagent system afforded the parent carbonyl compounds in moderate to quantitative yields under mild conditions. T
- Nishide, Kiyoharu,Nakamura, Daisaku,Yokota, Kouichi,Sumiya, Toshio,Node, Manabu,Ueda, Masaru,Fuji, Kaoru
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p. 393 - 404
(2007/10/03)
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- Mass spectra of 1,3-dithiaspiranes and 2-aryl-1,3-dithianes
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The mass spectra of 20 1,3-dithianes were studied. The fragmentation patterns including the loss of 74 u and 107 u and clearage of the substituent at C-2 depended strongly on the nature of the substituents at that position. 2,2-Diphenyl-1,3-dithiane under
- Shiue,Lin,Kuo,Chen
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p. 461 - 465
(2007/10/02)
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- Anodic gem-Difluorination of Dithioacetals
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Anodic desulfurization of dithioacetals of ketones in the presence of Et3N*3HF provided the corresponding gem-difluorocompounds while dithioacetals of aromatic and aliphatic aldehydes gave gem-difluorothioethers and monofluoro thioether, respectively.
- Yoshiyama, Tomonori,Fuchigami, Toshio
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p. 1995 - 1998
(2007/10/02)
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- FACILE SYNTHETIC METHODS OF ACETALS AND CROWN ETHERS FROM THE REACTION OF DIPHENYLDIAZOMETHANE WITH 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE IN THE PRESENCE OF ALCOHOLS
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The reaction of diphenyldiazomethane with 2,3-dichloro-5,6-dicyanobenzoquinone in the presence of alcohols and thiols gave the corresponding benzophenone acetals and thioacetals at 20-25 deg C in 1,2-dichloroethane.The mechanism of the reaction will be discussed.
- Oshima, Takumi,Nishioka, Ryoji,Nagai, Toshikazu
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p. 3919 - 3922
(2007/10/02)
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