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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 13
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Original Articles

An Efficient and Convenient Procedure for Preparation of 1,1-Diacetates from Aldehydes Catalysed by Expansive Graphite

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Pages 2261-2266 | Received 29 Nov 1996, Published online: 22 Aug 2006

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Read on this site (15)

Sedigheh Pargaleh Brojeni, Mojtaba Baghernejad, Dariush Saberi & Khodabakhsh Niknam. (2013) Silica immobilized sulfuric acid ([3-(propyl)sulfanyl]propyl]ester and N-propylsulfamic acid as recyclable catalysts for chemoselective synthesis of 1,1-diacetates. Green Chemistry Letters and Reviews 6:1, pages 69-75.
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Yurngdong Jahng & MotiurA. F. M. Rahman. (2006) Simple Synthesis of Geminal Diacetates (Acylals) of Aromatic Aldehydes. Synthetic Communications 36:9, pages 1213-1220.
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Tongshou Jin, Guoliang Feng, Mina Yang & Tongshuang Li. (2004) An Efficient and Practical Procedure for Synthesis of 1,1‐Diacetates from Aldehydes Catalyzed by Zirconium Sulfate Tetrahydrate–Silica Gel. Synthetic Communications 34:9, pages 1645-1651.
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Hossein Eshghi & Zinat Gordi. (2004) PHOSPHORUS PENTOXIDE-MONTMORILLONITE K-10 AS CATALYST FOR THE PREPARATION OF 1,1-DIACETATES UNDER SOLVENT-FREE CONDITIONS. Phosphorus, Sulfur, and Silicon and the Related Elements 179:7, pages 1341-1346.
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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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Abdol Reza Hajipour, Sepideh Khoee & ArnoldE. Ruoho. (2003) REGENERATION OF CARBONYL COMPOUNDS FROM OXIMES, HYDRAZONES, SEMICARBAZONES, ACETALS, 1,1-DIACETATES, 1,3-DITHIOLANES, 1,3-DITHIANES AND 1,3-OXATHIOLANES. Organic Preparations and Procedures International 35:6, pages 527-581.
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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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Babak Karimi, Gholam-Reza Ebrahimian & Hassan Seradj. (2002) HIGHLY EFFICIENT AND CHEMOSELECTIVE CONVERSION OF ALDEHYDES TO ACYLALS CATALYZED WITH TUNGSTEN HEXACHLORIDE (WCl6). Synthetic Communications 32:5, pages 669-673.
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Habib Firouzabadi, Nasser Iranpoor & Hassan Hazarkhani. (2001) Silica Chloride (Sio2-Cl) Promotes Highly Efficient Transformation of Acylals to Dithianes, Dithiolanesm, and Oxathiolanes. Phosphorus, Sulfur, and Silicon and the Related Elements 176:1, pages 165-171.
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I. Mohammadpoor-baltork & H. Aliyan. (1999) Bismuth (III) Chloride1; an Efficient and Selective Catalyst for Deprotection of 1,1-Diacetates. Synthetic Communications 29:16, pages 2741-2746.
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Tong-Shou Jin, Tong-Shuang Li, Zhan-Hui Zhang & Yan-Jun Yuan. (1999) Synthesis Of Diacetals By Condensation Of Carbonyl Compounds With Bis(Hydrox Ymethyl)-1,3-Propanediol Catalysed By Expansive Graphite. Synthetic Communications 29:9, pages 1601-1606.
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Tong-Shuang Li, Zhan-Hui Zhang & Yong-Jian Gao. (1998) A Rapid Preparation of Acylals of Aldehydes Catalysed by Fe3+-Montmorillonite. Synthetic Communications 28:24, pages 4665-4671.
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T.S. Jin, Y.R. Ma, Z.H. Zhang & T.S. Li. (1998) AN EFFICIENT AND FACILE PROCEDURE FOR DEPROTECTION OF 1,1-DIACETATES USING ANHYDROUS FERROUS SULFATE. Organic Preparations and Procedures International 30:4, pages 463-466.
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Tong-Shou Jin, Tong-Shuang Li & Yong-Tao Gao. (1998) A Facile Preparation of Methoxymethyl Ethers of Primary and Secondary Alcohols with Dimethoxymethane Catalysed by Expansive Graphite. Synthetic Communications 28:5, pages 837-841.
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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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Sándor B. Ötvös, István Pálinkó & Ferenc Fülöp. (2019) Catalytic use of layered materials for fine chemical syntheses. Catalysis Science & Technology 9:1, pages 47-60.
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Richard C. LarockRichard C. Larock & Tuanli Yao. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 85 .
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Mohsen Esmaeilpour, Ali Reza Sardarian & Jaber Javidi. (2012) Schiff base complex of metal ions supported on superparamagnetic Fe3O4@SiO2 nanoparticles: An efficient, selective and recyclable catalyst for synthesis of 1,1-diacetates from aldehydes under solvent-free conditions. Applied Catalysis A: General 445-446, pages 359-367.
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Farhad Shirini & Omid Goli Jolodar. (2012) Introduction of N-sulfonic acid poly(4-vinylpyridinum) chloride as an efficient and reusable catalyst for the chemoselective 1,1-diacetate protection and deprotection of aldehydes. Journal of Molecular Catalysis A: Chemical 356, pages 61-69.
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Nader Ghaffari Khaligh & Farhad Shirini. (2011) Preparation, characterization and use of poly(4-vinylpyridinium) hydrogen sulfate salt as an eco-benign, efficient and reusable solid acid catalyst for the chemoselective 1,1-diacetate protection and deprotection of aldehydes. Journal of Molecular Catalysis A: Chemical 348:1-2, pages 20-29.
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Giovanni Sartori & Raimondo Maggi. (2010) Update 1 of: Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis. Chemical Reviews 110:3.
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S. A. Lermontov & L. L. Yurkova. (2010) Solid superacids as catalysts for the synthesis of acylals from aldehydes and acetic anhydride. Russian Chemical Bulletin 57:12, pages 2561-2563.
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Geng-Chen Li. (2008) Synthesis of 14-aryl-14 H -dibenzo[ a,j ]xanthene Derivatives Catalysed by Expanded Graphite under Solvent-Free Condition . Journal of Chemical Research 2008:8, pages 484-485.
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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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Liang Yin, Zhan-Hui Zhang & Yong-Mei Wang. (2007) A stable intermediate: a new insight into the mechanism of Lewis acids-promoted formation of acylals from aldehydes. Tetrahedron Letters 48:17, pages 3119-3122.
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Andrea Komlósi, Ernő Kuzmann, Noémi M. Nagy, Zoltán Homonnay, Shiro Kubuki & József Kónya. (2024) Incorporation of Fe in the interlayer of Na-bentonite via treatment with FeCl 3 in acetone . Clays and Clay Minerals 55:1, pages 89-95.
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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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Motiur A. F. M. Rahman & Yurngdong Jahng. (2006) Preparation of Geminal Diacylates (Acylals) of Aldehydes – Scope and Reactivity of Aldehydes with Acid Anhydrides. European Journal of Organic Chemistry 2007:2, pages 379-383.
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Hui Wu, Yang Shen, Li-yan Fan, Yu Wan & Da-qing Shi. (2006) Solid silica sulfuric acid (SSA) as a novel and efficient catalyst for acetylation of aldehydes and sugars. Tetrahedron 62:34, pages 7995-7998.
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Vinod T. Kamble, Vasant S. Jamode, Neeta S. Joshi, Ankush V. Biradar & Rameshchandra Y. Deshmukh. (2006) An efficient method for the synthesis of acylals from aldehydes using silica-supported perchloric acid (HClO4–SiO2). Tetrahedron Letters 47:31, pages 5573-5576.
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Tong-Shou Jin, Ying Zhao, Li-Bin Liu & Tong-Shuang Li. (2019) A Rapid and Efficient Procedure for Deprotection of 1,1-diacetates Catalysed by Silica Sulfate. Journal of Chemical Research 2005:7, pages 438-439.
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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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Hongying Niu, Xinying Zhang, Haiming Guo & Jianji Wang. (2019) A mild and efficient deprotection of geminal diacetates catalysed by FeCl 3 ·6H 2 O in ionic liquid . Journal of Chemical Research 2004:11, pages 764-765.
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Giovanni Sartori, Roberto Ballini, Franca Bigi, Giovanna Bosica, Raimondo Maggi & Paolo Righi. (2003) Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis. Chemical Reviews 104:1, pages 199-250.
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Tong-Shou Jin, Guang Sun, Yan–Wei Li & Tong-Shuang Li. (2019) A Facile and Efficient Procedure for Deprotection of 1,1-Diacetates Catalysed by H 2 NSO 3 H . Journal of Chemical Research 2003:1, pages 30-32.
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Habib Firouzabadi, Nasser Iranpoor & Hamid Reza Shaterian. (2002) 2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO) as a Versatile, Efficient, and Chemoselective Catalyst for the Acetalization and Transacetalization of Carbonyl Compounds, the Preparation of Acetonides from Epoxides and Acylals (1,1-Diacetates) from Aldehydes. Bulletin of the Chemical Society of Japan 75:10, pages 2195-2205.
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Noémi M. Nagy, Márta A. Jakab, József Kónya & Sándor Antus. (2002) Convenient preparation of 1,1-diacetates from aromatic aldehydes catalysed by zinc-montmorillonite. Applied Clay Science 21:3-4, pages 213-216.
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Tong-Shou Jin, Xu Sun & Tong-Shuang Li. (2019) TiO 2 /SO 4 2- : A Facile and Efficient Catalyst for Deprotection of 1,1-diacetates . Journal of Chemical Research 2000:3, pages 128-129.
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Tong-Shou Jin, Yan-Ran Ma, Xu Sun, Dan Liang & Tong-Shuang Li. (2019) Facile Preparation of 1,1-Diacetates from Aldehydes with Acetic Anhydride Catalysed by TiO 2 /SO 4 2- solid superacid . Journal of Chemical Research 2000:2, pages 96-97.
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Iraj Mohammadpoor-Baltork & Hamid Aliyan. (2019) Aluminium Chloride: A Mild and Efficient Catalyst for Selective Deprotection of 1,1-Diacetates. Journal of Chemical Research 23:4, pages 272-273.
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Roberto Ballini, Marco Bordoni, Giovanna Bosica, Raimondo Maggi & Giovanni Sartori. (1998) Solvent free synthesis and deprotection of 1,1-diacetates over a commercially available zeolite Y as a reusable catalyst. Tetrahedron Letters 39:41, pages 7587-7590.
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Tommy Iliefski, Shiming Li & Knut Lundquist. (1998) Synthesis of cinnamaldehydes, esters of cinnamic acids and acylals of cinnamaldehydes by oxidation of arylpropenes with 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ). Tetrahedron Letters 39:16, pages 2413-2416.
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T.‐S. JIN, G.‐Y. DU, Z.‐H. ZHANG & T.‐S. LI. (2010) ChemInform Abstract: An Efficient and Convenient Procedure for the Preparation of 1,1‐ Diacetates from Aldehydes Catalyzed by Expansive Graphite.. ChemInform 28:37.
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