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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 29, 1999 - Issue 16
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Original Articles

Bismuth (III) Chloride1; an Efficient and Selective Catalyst for Deprotection of 1,1-Diacetates

I. Mohammadpoor-baltork Department of Chemistry, Esfahan University, Esfahan, 81744, Iran
&
H. Aliyan Department of Chemistry, Esfahan University, Esfahan, 81744, Iran
Pages 2741-2746 | Received 18 Sep 1998, Published online: 25 Sep 2007

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Gaurav Bartwal, Mohit Saroha & Jitender M. Khurana. (2018) Nickel boride mediated chemoselective deprotection of 1,1-diacetates to aldehydes and deprotection with concomitant reduction to alcohols at ambient temperature. Synthetic Communications 48:1, pages 97-103.
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Firouzeh Nemati, Mehrnoosh Golmohammadi Afkham & Ali Elhampour. (2014) Nano-Fe3O4-encapsulated silica particles bearing sulfonic acid groups as a magnetically separable catalyst for green synthesis of 1,1-diacetates. Green Chemistry Letters and Reviews 7:1, pages 79-84.
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Bandita Datta & M.A. Pasha. (2011) Chemoselective Protection and Deprotection of Aldehydes Using Solid Supported Reagent (Silica Chloride) Under Solvent-Free Conditions. Synthetic Communications 41:8, pages 1160-1166.
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Abdolhamid Bamoniri, Arash Ghorbani-Choghamarani & Bi Bi Fatemeh Mirjalili. (2011) A New and Efficient Procedure for the Production of 1,1-Diacetate from Corresponding Aldehydes Promoted by Silica Chromate (SiO2-O-CrO2-O-SiO2). Phosphorus, Sulfur, and Silicon and the Related Elements 186:2, pages 381-388.
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Fuyi Zhang, Hong Liu, Qing-Ju Zhang, Yu-Fen Zhao & Feng-Ling Yang. (2010) Silica Phosphoric Acid: An Efficient and Recyclable Catalyst for the Solvent-Free Synthesis of Acylals and Their Deprotection in MeOH. Synthetic Communications 40:21, pages 3240-3250.
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Hadi Adibi, Ahmad Reza Massah, Mohammad Bagher Majnooni, Sherita Shahidi, Maryam Afshar, Ramin Abiri & Hamid Javaherian Naghash. (2010) Synthesis, Characterization, and Antimicrobial Evaluation of Sulfonamides Containing N-Acyl Moieties Catalyzed by Bismuth(III) Salts Under Both Solvent and Solvent-Free Conditions. Synthetic Communications 40:18, pages 2753-2766.
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Majid M. Heravi, Fatemeh Derikvand & Fatemeh F. Bamoharram. (2006) Dodecatungstophosphoric Acid (H3PW12O40): A Novel and Efficient Recyclable Catalyst for Synthesis of 1,1‐Diacetates from Aromatic Aldehydes in Solvent‐Free System and Their Deprotection. Synthetic Communications 36:21, pages 3109-3115.
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G. P. Romanelli, J. C. Autino, G. Baronetti & H. J. Thomas. (2004) A Fast and Efficient Deprotection of Aldehydes from Acylals Using a Wells‐Dawson Heteropolyacid Catalyst (H6P2W18O62 · 24H2O). Synthetic Communications 34:21, pages 3909-3914.
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BiBi Fatemeh Mirjalili, Mohammad Ali Zolfigol & Abdolhamid Bamoniri. (2004) AN EFFICIENT CONVERSION OF ALDEHYDES TO THEIR CORRESPONDING ACYLALS WITH P2O5/SiO2 UNDER MILD CONDITION. Phosphorus, Sulfur, and Silicon and the Related Elements 179:1, pages 19-24.
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Adyl Oussaid, Fatima Benyaqad, Boualem Oussaid & Bernard Garrigues. (2003) Ene Réaction et Réaction de Substitution sur Des Hétérocycles Catalysées par les Sels de Bi(III). Phosphorus, Sulfur, and Silicon and the Related Elements 178:7, pages 1605-1616.
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Mohammad Ali Zolfigol, Mohammad Hassan Zebarjadian, Iraj Mohammadpoor-Baltork & Mojtaba Shamsipur. (2002) DEPROTECTION OF 1,1-DIACETATES WITH [NO+ ⋅ CROWN ⋅ H(NO3)2 −]. Synthetic Communications 32:18, pages 2803-2808.
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I. Mohammadpoor-Baltork & A. R. Khosropour. (2002) Bi(III) SALTS AS NEW CATALYSTS FOR THE SELECTIVE CONVERSION OF TRIMETHYLSILYL AND TETRAHYDROPYRANYL ETHERS TO THEIR CORRESPONDING ACETATES AND FORMATES. Synthetic Communications 32:15, pages 2433-2439.
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Iraj Mohammadpoor-Baltork, Bahram Kharamesh & Sadegh Kolagar. (2002) EFFICIENT DEPROTECTION OF TETRAHYDROPYRANYL ETHERS BY BISMUTH(III) SALTS. Synthetic Communications 32:11, pages 1633-1637.
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I. Mohammadpoor-Baltork, A. R. Khosropour & H. Aliyan. (2001) EFFICIENT CONVERSION OF EPOXIDES TO 1,3-DIOXOLANES CATALYZED BY BISMUTH(III) SALTS. Synthetic Communications 31:22, pages 3411-3416.
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H. Firouzabadi, I. Mohammadpoor-Baltork & S. Kolagar. (2001) A RAPID, SELECTIVE, AND EFFICIENT METHOD FOR DEPROTECTION OF SILYL ETHERS CATALYZED BY BISMUTH(III) SALTS. Synthetic Communications 31:6, pages 905-909.
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I. Mohammadpoor-Baltork, S. Tangestaninejad, H. Aliyan & V. Mirkhani. (2000) Bismuth(III) Chloride (BiCl3); An Efficient Catalyst for Mild, Regio- and Stereoselective Cleavage of Epoxides with Alcohols, Acetic Acid and Water. Synthetic Communications 30:13, pages 2365-2374.
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Articles from other publishers (25)

Sobhan Rezayati & Ali Ramazani. (2020) Metal-based Lewis acid catalysts for conversion of a variety of aldehydes with acetic anhydride to gem 1,1-diacetates. Research on Chemical Intermediates 46:7, pages 3757-3799.
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Bhagirath Limbani, Dhananjoy Mondal & Smritilekha Bera. 2020. Green Sustainable Process for Chemical and Environmental Engineering and Science. Green Sustainable Process for Chemical and Environmental Engineering and Science 203 241 .
. 2014. Greene's Protective Groups in Organic Synthesis. Greene's Protective Groups in Organic Synthesis 554 685 .
Nader Ghaffari Khaligh & Farhad shirini. (2013) Ultrasound assisted the chemoselective 1,1-diacetate protection and deprotection of aldehydes catalyzed by poly(4-vinylpyridinium)hydrogen sulfate salt as a eco-benign, efficient and reusable solid acid catalyst. Ultrasonics Sonochemistry 20:1, pages 19-25.
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Farhad Shirini, Zahra Neyestani & Masoumeh Abedini. (2009) KBrO3/MoO3: An efficient reagent system for the oxidative deprotection of semicarbazones, 1,1-diacetates and acetals. Chinese Chemical Letters 20:5, pages 514-518.
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Iraj Mohammadpoor-Baltork, Majid Moghadam, Shahram Tangestaninejad, Valiollah Mirkhani & Arsalan Mirjafari. (2008) 12-Tungstophosphoric acid supported on inorganic oxides as heterogeneous and reusable catalysts for the selective preparation of alkoxymethyl ethers and their deprotections under different reaction conditions. Polyhedron 27:12, pages 2612-2624.
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Razieh FAZAELI & Hamid ALIYAN. (2008) Cu3/2PMo12O40/SiO2: A Heterogeneous, Eco-friendly and Reusable Catalyst for the Solvent-Free Catalytic Preparation of 1,1-Diacetates from Aldehydes. Chinese Journal of Catalysis 29:1, pages 10-14.
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Razieh Fazaeli, Shahram Tangestaninejad & Hamid Aliyan. (2007) Highly efficient conversion of aldehydes to geminal diacetates (solvent-free) and their deprotection using facile and reusable molybdenum and tungsten polyoxometalates. Applied Catalysis A: General 318, pages 218-226.
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Uday V. Desai, T.S. Thopate, D.M. Pore & P.P. Wadgaonkar. (2006) An efficient, solvent-free method for the chemoselective synthesis of acylals from aldehydes and their deprotection catalyzed by silica sulfuric acid as a reusable solid acid catalyst. Catalysis Communications 7:7, pages 508-511.
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Ramin Ghorbani-Vaghei, Safar-Ali Akbari, Mohammad A. Zolfigol, BiBi Fatemeh Mirjalili & Abdolhamid Bamoniri. (2006) Solid-state conversion of 1,1-diacetates with N,N′-dibromo-N,N′-1,2-ethanediylbis(p-toluenesulfonamide) to aldehydes. Mendeleev Communications 16:1, pages 55-56.
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Hossein Eshghi & Parvaneh Shafieyoon. (2005) P 2 O 5 /SiO 2 as an Efficient Reagent for Selective Deprotection of 1,1-Diacetates under Solvent-Free Conditions . Journal of the Chinese Chemical Society 52:1, pages 155-157.
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Zhan-Hui Zhang, Liang Yin, Yi Li & Yong-Mei Wang. (2005) A practical and efficient procedure for the cleavage of acylals to aldehydes catalyzed by indium tribromide in water. Tetrahedron Letters 46:5, pages 889-893.
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Veerababurao Kavala & Bhisma K. Patel. (2005) Reinvestigation of the Mechanism of gem ‐Diacylation: Chemoselective Conversion of Aldehydes to Various gem ‐Diacylates and Their Cleavage under Acidic and Basic Conditions . European Journal of Organic Chemistry 2005:2, pages 441-451.
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Zhan-Hui Zhang. (2019) Indium tribromide/[bmim]PF 6 : A novel and recyclable catalytic system for the deprotection of 1,1-diacetates . Journal of Chemical Research 2004:11, pages 753-755.
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Axel Jacobi von Wangelin. 2004. Transition Metals for Organic Synthesis. Transition Metals for Organic Synthesis 379 394 .
G Smitha & Ch.Sanjeeva Reddy. (2003) A facile and efficient ZrCl 4 catalyzed conversion of aldehydes to geminal-diacetates and dipivalates and their cleavage. Tetrahedron 59:48, pages 9571-9576.
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. (2003) Bismuth(Ⅲ) Nitrate Pentahydrate Bi(NO 3 ) 3 ·5H 2 O: An Inexpensive and Mild Reagent for the Efficient and Clean Oxidation of Thiols to Disulfides . Bulletin of the Korean Chemical Society 24:7, pages 885-886.
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Michael B. Smith. 2003. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 90 114 .
Iraj Mohammadpoor-Baltork, Mohammad Mehdi Khodaei & Kobra Nikoofar. (2003) Bismuth(III) nitrate pentahydrate: a convenient and selective reagent for conversion of thiocarbonyls to their carbonyl compounds. Tetrahedron Letters 44:3, pages 591-594.
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Nicholas M. Leonard, Laura C. Wieland & Ram S. Mohan. (2002) Applications of bismuth(III) compounds in organic synthesis. Tetrahedron 58:42, pages 8373-8397.
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Iraj Mohammadpoor-Baltork & Ahmad Khosropour. (2001) Bi(TFA)3 and Bi(OTf)3 Catalyzed Conversions of Epoxides to Thiiranes with Ammonium Thiocyanate and Thiourea under Non-Aqueous Conditions. Molecules 6:12, pages 996-1000.
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Iraj Mohammadpoor-Baltork, Ahmad Reza Khosropour & Hamid Aliyan. (2019) A Convenient and Chemoselective Acetylation and Formylation of Alcohols and Phenols Using Acetic Acid and Ethyl Formate in the Presence of Bi(III) Salts. Journal of Chemical Research 2001:7, pages 280-282.
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Iraj Mohammadpoor-Baltork, Hamid Aliyan & Ahmad Reza Khosropour. (2001) Bismuth(III) salts as convenient and efficient catalysts for the selective acetylation and benzoylation of alcohols and phenols. Tetrahedron 57:27, pages 5851-5854.
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. 2001. Organobismuth Chemistry. Organobismuth Chemistry 571 614 .
I. Mohammadpoor‐Baltork & H. Aliyan. (2010) ChemInform Abstract: Bismuth(III) Chloride; an Efficient and Selective Catalyst for Deprotection of 1,1‐Diacetates.. ChemInform 30:40.
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