- Application of poly(Vinylbenzyltrimethylammonium tribromide) resin as an efficient polymeric catalyst in the acetalization and diacetylation of benzaldehydes
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The applications of a new supported tribromide reagent (poly(vinylbenzyltrimethylammonium tribromide) resin) were reported. This supported tribromide resin was used as a catalyst in the acetalization and diacetylation of benzaldehydes under mild conditions with high efficiency. The effects of solvents, and amount of the supported tribromide resin on the reactions were investigated. Under the optimal conditions, most of acetal and 1,1-diacetates of benzaldehydes were selectively obtained in excellent yields.
- Han, Bingbing,Hu, Junjun,Li, Xianwei,Zheng, Zubiao
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supporting information
p. 287 - 293
(2021/04/28)
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- Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents
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A variety of functionalized triarylmethane and 1,1-diarylalkane derivatives were prepared via a transition-metal-free, one-pot and two-step procedure, involving the reaction of various benzal diacetates with organozinc reagents. A sequential cross-coupling is enabled by changing the solvent from THF to toluene, and a two-step SN1-type mechanism was proposed and evidenced by experimental studies. The synthetic utility of the method is further demonstrated by the synthesis of several biologically relevant molecules, such as an anti-tuberculosis agent, an anti-breast cancer agent, a precursor of a sphingosine-1-phosphate (S1P) receptor modulator, and a FLAP inhibitor.
- Wei, Baosheng,Ren, Qianyi,Bein, Thomas,Knochel, Paul
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supporting information
p. 10409 - 10414
(2021/03/26)
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- The studies on chemoselective promiscuous activity of hydrolases on acylals transformations
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Chemoselective, mild and convenient protocol for the hydrolysis of the synthetically relevant acylals via promiscuous enzyme-catalyzed hydrolysis has been developed. It has been shown that promiscuous activity of the used hydrolases dominates their native activity related with carboxylic esters hydrolysis. The main advantage of the present methodology is that it can be conducted under neutral conditions at room temperature. Moreover, complete deprotection of acylals takes place within 10–20 min. Developed protocol can be used with compounds having a variety of hydrolytic labile groups since the cleavage is proceeded under neutral conditions and occurs exclusively on acylal moiety. Further this protocol was extended by the tandem Passerini multicomponent reaction leading to the α-acetoxy amides using acylals as the surrogates of the carbonyl components to P-MCR.
- Koszelewski, Dominik,Ostaszewski, Ryszard
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- N-Propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) as a green and reusable heterogeneous nanocatalyst for the chemoselective preparation and deprotection of acylals
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Abstract: N-propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) was simply synthesized and used as a highly efficient, environmentally friendly, and chemoselective catalyst for the synthesis of 1,1-diacetates (acylals) from the one-pot condensation reaction of various aromatic aldehydes with acetic anhydride, in high yield of products (86–96%) and short reaction time (20–60?min) under solvent-free conditions at room temperature. In addition to these results, we further studied the possibility of deprotection of the resulting acylals into benzaldehyde derivatives in this catalytic system by the addition of water. More importantly, noteworthy advantages of this study are non-use of toxic organic solvents and catalysts, simple work-up procedure, short reaction time, high yield of products, and recovery and reusability of MNPs-PSA by an external magnet. Graphical Abstract: A simple and highly efficient procedure for the protection of various aldehydes with acetic anhydride in the presence of N-propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) is reported. We further studied the possibility of deprotection of the resulting acylals into benzaldehyde derivatives in this catalytic system by the addition of water as a green solvent. The catalyst was reused several times without loss of its catalytic activity.
- Sajjadifar, Sami,Nasri, Parastoo
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p. 6677 - 6689
(2017/10/06)
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- Formation of benzylidenes-diacetates catalyzed by activated zeolite "LZY-562" and clay (K10/ZnCl2): An unexpected functional selectivity
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Activated zeolites LZY-562 and clay montmorillonite K10 at room temperature without solvent catalyzes the synthesis of benzylidenesdiacetates from carbonyl compounds. A chemoselectivity was observed between aldehydes and ketones, between the different aldehydes and ketones as well.
- Dokari,Hammadi,Benferrah,Rachedi
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p. 1973 - 1976
(2015/12/01)
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- Green procedures for the chemoselective synthesis of acylals and their cleavage promoted by recoverable sulfonic acid based nanoporous carbon (CMK-5-SO3H)
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A selective synthesis of gem-diacetates from the reaction of aldehydes and acetic anhydride in the presence of recyclable nanoporous solid sulfonic acid (CMK-5-SO3H) under solvent-free reaction conditions is reported. The catalyst was also found to be highly active for deprotection of resulting acylals in water. [Figure not available: see fulltext.]
- Zareyee, Daryoush,Mirzajanzadeh, Ehsan,Khalilzadeh, Mohammad Ali
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p. 1229 - 1234
(2015/10/06)
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- An efficient method for synthesis of acylals from aldehydes using multi-walled carbon nanotubes functionalized with phosphonic acid (MWCNTs-C-PO3H2)
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MWCNTs-C-PO3H2 has been used as an efficient, heterogeneous and reusable nanocatalyst for synthesis of acylals from aldehydes under solvent-free conditions at room temperature. A wide range of aldehydes was studied and corresponding products were obtained in good to excellent yields in short reaction times. Nanocatalyst can be easily recovered by centrifuge and reused for subsequent reactions for at least five times without deterioration in catalytic activity. The major advantages of the present method are high yields, short reaction time, recyclable catalyst and solvent-free reaction conditions at room temperature.
- Dehghani, Farzaneh,Sardarian, Ali Reza,Doroodmand, Mohammad Mehdi
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p. 1630 - 1634
(2015/01/09)
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- Chemoselective synthesis of geminal diacetates (acylals) using eco-friendly reusable propylsulfonic acid based nanosilica (SBA-15-Ph-PrSO3H) under solvent-free conditions
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An expeditious method for the acetylation of aldehydes by mesoporous solid sulfonic acid (SBA-15-Ph-PrSO3H) under solvent-free reaction conditions was described. The route furnished selectively and in excellent yields the corresponding 1,1-diacetates starting from aldehydes and acetic anhydride using the environmentally friendly catalyst. The catalyst was found to be highly active and selective and could be recycled several times.
- Zareyee, Daryoush,Moosavi, Sayed M.,Alaminezhad, Alireza
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p. 227 - 231
(2013/08/23)
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- Polystyrene-supported TiCl4 as a novel, efficient and reusable polymeric Lewis acid catalyst for the chemoselective synthesis and deprotection of 1,1-diacetates under eco-friendly conditions
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Copolymer beads of styrene and divinylbenzene (5-7%) were synthesized and combined with titanium tetrachloride in CS2 to form a stable complex. The PS/TiCl4 complex was used as a mild and efficient polymer-supported Lewis acid catalyst for the preparation of 1,1-diacetates from various types of aldehydes under heterogeneous conditions at room temperature. Deprotection of the resulting 1,1-diacetates has also been achieved using the same catalyst in methanol. This new protocol has the advantages of easy availability, stability, reusability of the eco-friendly catalyst, high to excellent yields, chemoselectivity, simple experimental and work-up procedure. Moreover, this polymeric catalyst could be recovered easily and reused several times without significant loss in activity.
- Rahmatpour, Ali,Mohammadian, Sara
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p. 912 - 919
(2013/10/22)
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- Schiff base complex of metal ions supported on superparamagnetic Fe 3O4@SiO2 nanoparticles: An efficient, selective and recyclable catalyst for synthesis of 1,1-diacetates from aldehydes under solvent-free conditions
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We report a new multistep method for preparing functionalized superparamagnetic Fe3O4@SiO2 possessing high saturation magnetization. During the first step, Fe3O 4@SiO2 nanosphere core-shell is synthesized using nano-Fe3O4 as the core, TEOS as the silica source and PVA as the surfactant. Then, Schiff base complex of metal is synthesized from the reaction between Schiff base and metal acetates [Co(OAc)2, Mn(OAc)2, Ni(OAc)2, Cu(OAc)2, Hg(OAc) 2, Cr(OAc)3 and Cd(OAc)2] on the Fe 3O4@SiO2 surface. The structural and magnetic properties of functionalized magnetic silica are identified by transmission electron microscopy (TEM) and vibrating sample magnetometer (VSM) instruments. Moreover, functionalized Fe3O4@SiO2 possessed a superparamagnetic characteristic with saturation magnetization value of about 34 emu/g. NMR, FT-IR, elemental analysis and XRD were also used for the identification of these structures. The catalytic ability of Fe 3O4@SiO2/Schiff base complex of metal ions was found to be an efficient nanocatalyst for the conversion of aldehydes to their corresponding 1,1-diacetates compounds under mild and solvent-free conditions at room temperature. This method gives notable advantages such as excellent chemoselectivity, mild reaction condition, short reaction times and excellent yields. Also, the aforementioned nanocatalyst can be easily recovered by a magnetic field and reused for subsequent reactions for at least 5 times without noticeable deterioration in catalytic activity.
- Esmaeilpour, Mohsen,Sardarian, Ali Reza,Javidi, Jaber
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p. 359 - 367
(2013/02/21)
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- Preparation of silica-bonded propyl-diethylene-triamine-N-sulfamic acid as a recyclable catalyst for chemoselective synthesis of 1,1-diacetates
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A simple and efficient procedure for the preparation of silica-bonded propyl-diethylene-triamine-N-sulfamic acid (SPDTSA) by reaction of 3-diethylenetriamine-propylsilica (DTPS) and chlorosulfonic acid in chloroform is described. Silica-bonded propyl-diethylene-triamine-N-sulfamic acid is employed as a recyclable catalyst for the synthesis of 1,1-diacetates from aromatic aldehydes and acetic anhydride under mild and solvent-free conditions at room temperature. Catalyst could be recycled for several times without any additional treatment.
- Nouri Sefat, Maryam,Deris, Abdolah,Niknam, Khodabakhsh
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experimental part
p. 2361 - 2367
(2012/02/03)
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- Cobalt-catalyzed addition of azoles to alkynes
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A ternary catalytic system consisting of a cobalt salt, a diphosphine ligand, and a Grignard reagent promotes syn-addition of an azole C(2)-H bond across an unactivated internal alkyne with high chemo-, regio-, and stereoselectivities under mild conditions. Mechanistic experiments suggest that the reaction involves oxidative addition of the oxazolyl C-H bond to the cobalt center, alkyne insertion into the Co-H bond, and reductive elimination of the resulting diorganocobalt species.
- Ding, Zhenhua,Yoshikai, Naohiko
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supporting information; experimental part
p. 4180 - 4183
(2010/11/19)
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- Silica-bonded S-sulfonic acid as a recyclable catalyst for chemoselective synthesis of 1,1-diacetates
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A simple and efficient procedure for the preparation of silica-bonded S-sulfonic acid (SBSSA) by reaction of 3-mercaptopropylsilica (MPS) and chlorosulfonic acid in chloroform is described. This solid acid is employed as a recyclable catalyst for the synthesis of 1,1-diacetates from aromatic aldehydes and acetic anhydride under mild and solvent-free conditions at room temperature.
- Niknam, Khodabakhsh,Saberi, Dariush,Sefat, Maryam Nouri
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scheme or table
p. 4058 - 4062
(2009/10/11)
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- Cerium(IV) triflate-catalyzed selective gem-diacetylation of aldehydes with acetic anhydride
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It has been observed that a catalytic amount (0.1 mol%) of cerium(IV) triflate afforded geminal diacetates from aldehydes with acetic anhydride in toluene at ambient temperature. Ketones are not affected under these reaction conditions. The reaction is rapid and mild with good to high yields. Copyright Taylor & Francis Group, LLC.
- Bosco, J. W. John,Saikia, Anil K.
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- A facile and efficient conversion of aldehydes into 1,1-diacetates (acylals) using iron(III) fluoride as a novel catalyst
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Aldehydes are smoothly converted into the corresponding 1,1-diacetates (acylals) in high yields in the presence of a catalytic amount (0.1 mol-%) of iron(III) fluoride at room temperature. The noteworthy features of the present system are shorter reaction times, chemoselective protection of aldehydes, and solvent-free conditions. The procedure is especially useful for large-scale syntheses as the catalyst is highly effective from the view of activity, selectivity, reusability, and economy in the preparation of 1,1-diacetates (acylals). CSIRO 2007.
- Kamble,Tayade,Davane,Kadam
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p. 590 - 594
(2008/03/11)
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- A versatile and practical synthesis of 1,1-diacetates from aldehydes catalyzed by cyanuric chloride
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Structurally diverse aldehydes are successfully converted into 1,1-diacetates with acetic anhydride using cyanuric chloride as a mild, convenient and inexpensive catalyst under solvent-free conditions. The noteworthy features of the present system are shorter reaction times, and mild and solvent-free conditions. Furthermore, it offers chemoselective protection of aldehydes.
- Bandgar, Babasaheb P.,Joshi, Neeta S.,Kamble, Vinod T.
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p. 489 - 492
(2008/02/11)
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- A remarkable HBF4-SiO2-catalyzed synthesis of acylals from aldehydes under solvent-free conditions
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HBF4-SiO2 has been found to be an outstanding catalyst for the protection of carbonyl compounds as acylals under entirely solvent-free conditions. Some of the major advantages of this procedure are high yields, ease of operation, high chemoselectivity, high atom efficiency, and compatibility with other protecting groups. Georg Thieme Verlag Stuttgart.
- Kamble, Vinod T.,Bandgar, Babasaheb P.,Joshi, Neeta S.,Jamode, Vasant S.
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p. 2719 - 2722
(2008/02/11)
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- An efficient method for the synthesis of acylals from aldehydes using silica-supported perchloric acid (HClO4-SiO2)
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The synthesis of acylals from structurally diverse aldehydes has been performed in excellent yields under solvent-free conditions using HClO4-SiO2 as a mild, convenient, reusable, and heterogeneous catalyst. The procedure is operationally simple, environmentally benign and has the advantage of enhanced atom utilization. Furthermore, the catalyst can be recovered simply and reused efficiently a number of times without appreciable loss of activity.
- Kamble, Vinod T.,Jamode, Vasant S.,Joshi, Neeta S.,Biradar, Ankush V.,Deshmukh, Rameshchandra Y.
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p. 5573 - 5576
(2007/10/03)
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- An efficient and practical procedure for preparation of gem-diacetates from aldehydes catalysed by magnesium perchlorate
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A mild and efficient method for the preparation of grem-diacetates from aldehydes with acetic anhydride is described using a catalytic amount of magnesium perchlorate giving excellent yields under solvent-free conditions.
- Yang, Shu-Tao
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p. 199 - 202
(2007/10/03)
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- Zn(OTf)2.6H2O catalysed acylation of aldehydes: Preparation of 1,1-diacetates and α-chloroalkyl esters
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1,1-Diacetates (acylals) and α-chloroalkyl esters were prepared from carbonyl compounds with acylating reagents in the presence of 5% mol hexaaqua zinc triflate [Zn(OTf)2.6H2O] with good yields under mild reaction conditions.
- Su, Weike,Can, Jin
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- 1,3-Dibromo-5,5-dimethylhydantoin as catalyst for the conversion of aldehydes to their 1,1-diacetates (acetylals) under solvent-free and neutral conditions
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Highly efficient and mild acetylation of aldehydes with acetic anhydride catalysed by 1,3-dibromo-5,5-dimethylhydantoin (DBH) was performed under neutral conditions to produce corresponding 1,1-diacetates (acetylals) in good to excellent yields.
- Azarifar, Davood,Ghasemnejad, Hassan,Ramzanian-lehmali, Farhad
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p. 209 - 210
(2007/10/03)
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- Lithium chloride-assisted chemoselective conversion of aldehydes into geminal diacetates under solvent-free conditions
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A mixture of lithium chloride and acetic anhydride was used for converting aldehydes into geminal diacetates under solvent-free conditions in high yields. Copyright Taylor & Francis, Inc.
- Bosco, J.W. John,Purkayastha,Raju, B. Rama,Saikia, Anil K.
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p. 1301 - 1305
(2007/10/03)
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- Copper(II) tetrafluoroborate-catalyzed formation of aldehyde-1,1-diacetates
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Aldehyde 1,1-diacetates are farmed in excellent yields from aldehydes and acetic anhydride under solvent-free conditions at room temperature in short times in the presence of a catalytic amount of copper(II) tetrafluoroborate hydrate.
- Chakraborti, Asit K.,Thilagavathi, Ramasamy,Kumar, Raj
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p. 831 - 833
(2007/10/03)
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- Zinc tetrafluoroborate-catalyzed efficient conversion of aldehydes to geminal diacetates and cyanoacetates
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A trace of an aqueous solution of zinc tetrafluoroborate was demonstrated to catalyze the conversion of an aldehyde to its 1,1-diacetate by acetic anhydride without any solvent. A similar reaction of an aldehyde with a mixture of potassium cyanide and acetic anhydride in methylene chloride was also catalyzed by Zn(BF4)2 to provide the corresponding geminal cyanoacetate.
- Ranu, Brindaban C.,Dutta, Jyotirmoy,Das, Arijit
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p. 366 - 367
(2007/10/03)
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- Lithium trifluoromethanesulfonate (LiOTf) as a recyclable catalyst for highly efficient acetylation of alcohols and diacetylation of aldehydes under mild and neutral reaction conditions
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A variety of alcohols and aldehydes were reacted with acetic anhydride at room temperature in the presence of a catalytic amount of lithium triflate (LiOTf) to produce the corresponding esters and 1,1-diacetates, respectively, in good to excellent yields under essentially neutral reaction conditions. Sensitive functional groups such as PhCO2-, OMe, and OTBDMS ethers survived intact under the described reaction conditions.
- Karimi, Babak,Maleki, Jafar
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p. 4951 - 4954
(2007/10/03)
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- A facile method for the preparation and cleavage of 1,1-diacetates of aldehydes
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A convenient method for the preparation and cleavage of 1,1-diacetates of aldehydes is reported using AlCl3 as catalyst.
- Sabitha, Gowravaram,Abraham, Sunny,Ramalingam,Yadav
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p. 144 - 146
(2007/10/03)
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- Indium trichloride catalyzed chemoselective conversion of aldehydes to gem-diacetates
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Aldehydes are chemoselectively converted into the corresponding gem-diacetates at ambient temperature in high to quantitative yields using a catalytic amount of indium (III) chloride. The deprotection of the resulting gem-diacetates is achieved using the same catalyst in the presence of water.
- Yadav,Subba Reddy,Srinivas, Ch.
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p. 1175 - 1180
(2007/10/03)
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- Indium trichloride catalyzed chemoselective conversion of aldehydes to gem-diacetates
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Aldehydes are chemoselectively converted into the corresponding gem-diacetates at ambient temperature in high to quantitative yields using a catalytic amount of indium(III) chloride. The deprotection of the resulting gem-diacetates is achieved using the s
- Yadav,Reddy, B. V. Subba,Srinivas
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p. 2169 - 2174
(2007/10/03)
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- LiBF4-mediated conversion of aldehydes to gem-diacetates
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An efficient and highly selective method for the conversion of aldehydes to gem-diacetates is described using lithium tetrafluoroborate under mild reaction conditions. Due to the neutral reaction conditions, this method is compatible with acid-sensitive p
- Yadav, Jhillu S.,Reddy, Basi V. S.,Venugopal, Chenna,Ramalingam
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p. 604 - 606
(2007/10/03)
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- A novel and efficient conversion of aldehydes to 1,1-diacetates catalyzed with FeCl3/SiO2 under microwave irradiation
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1,1-Diacetates (3) are effectively synthesized in few minutes by acylation reaction of aldehydes with acetic anhydride in the presence of FeCl3/SiO2 under microwave irradiation.
- Wang, Cunde,Li, Minghua
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p. 3469 - 3473
(2007/10/03)
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- Efficient and selective protection of aldehydes as geminal diacetates using LiBr
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A variety of aldehydes react with acetic anhydride in presence of lithium bromide at room temperature to afford the corresponding 1,1-diacetates in quantitative yields within a few hours of reaction time.
- Kumar, H. M. Sampath,Reddy, B. V. Subba,Reddy, P. Thirupathi,Yadav, J. S.
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- Diacetates from aldehydes in the presence of zeolites
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An easy preparation of diacetates from aldehydes and acetic anhydride in the presence of zeolites is reported.
- Pereira,Gigante,Marcelo-Curto,Carreyre,Perot,Guisnet
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p. 1077 - 1078
(2007/10/02)
-