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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 19
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Original Articles

An Efficient and Facile Procedure for the Deprotection of 1,1-Diacetates Catalysed by Expansive Graphite

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Pages 3379-3383 | Received 23 Feb 1997, Published online: 22 Aug 2006

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Read on this site (12)

Mohammad Reza Nabid, Seyed Jamal Tabatabaei Rezaei & Mahvash Abedi. (2010) Conjugate Polymer-Supported Acid Catalysts: An Efficient and Reusable Catalyst for the Synthesis of Geminal Diacetates (Acylals) Under Solvent-Free Conditions. Synthetic Communications 41:2, pages 191-199.
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GangadharA. Meshram & VishvanathD. Patil. (2010) Chemoselective Synthesis of 1,1-Diacetates from Aldehydes Using Anhydrous Cobalt(II) Bromide Under Solvent-Free Conditions. Synthetic Communications 40:3, pages 442-449.
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Anil Saini, Sanjay Kumar & Jagir. S. Sandhu. (2007) RuCl3 · xH2O: A New Efficient Catalyst for Facile Preparation of 1,1‐Diacetates from Aldehydes. Synthetic Communications 38:1, pages 106-113.
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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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M.M. Lakouraj, M. Tajbakhsh, V. Khojasteh & M.H. Gholami. (2004) CARO'S ACID SUPPORTED ON SILICA GEL. PART VI. A MILD REAGENT FOR REGENERATION OF CARBONYL COMPOUNDS FROM ACETALS, KETALS, AND 1,1-DIACETATES. Phosphorus, Sulfur, and Silicon and the Related Elements 179:12, pages 2645-2651.
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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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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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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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Farhad SHIRINI & Nader Ghaffari KHALIGH. (2013) A succinimide-N-sulfonic acid catalyst for acetylation reactions in absence of a solvent. Chinese Journal of Catalysis 34:4, pages 695-703.
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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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Maryam Yadegari, Majid Moghadam, Shahram Tangestaninejad, Valiollah Mirkhani & Iraj Mohammadpoor-Baltork. (2012) High-valent titanium(IV)salophen: An efficient catalyst for rapid conversion of aldehydes to 1,1-diacetates with acetic anhydride. Inorganica Chimica Acta 388, pages 102-105.
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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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Maryam Moosavifar, Shahram Tangestaninejad, Majid Moghadam, Valiollah Mirkhani & Iraj Mohammadpoor-Baltork. (2011) Host (nanocavity of zeolite-Y)–guest (molybdophosphoric acid) nanocomposite materials: An efficient catalyst for solvent-free synthesis and deprotection of 1,l-diacetates. Comptes Rendus Chimie 14:10, pages 953-956.
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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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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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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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Ajayan Vinu, Josena Justus, Veerappan Vaithilingam Balasubramanian, Shivappa Basappa Halligudi, Katsuhiko Ariga & Toshiyuki Mori. (2008) Synthesis of Fructone and Acylal Using Hexagonally Ordered Mesoporous Aluminosilicate Catalyst. Collection of Czechoslovak Chemical Communications 73:8-9, pages 1112-1124.
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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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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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Jianmin Wang, Liang Yan, Guang Qian, Keli Yang, Haitao Liu & Xiaolai Wang. (2006) Heteropolyacid encapsulated into mesoporous silica framework for an efficient preparation of 1,1-diacetates from aldehydes under a solvent-free condition. Tetrahedron Letters 47:47, pages 8309-8312.
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Masoud Salavati-Niasari & Samansa Hydarzadeh. (2005) An effective method for the selective synthesis of geminal diacetates (acylals) from aromatic aldehydes using alumina-supported InCl3. Journal of Molecular Catalysis A: Chemical 237:1-2, pages 254-258.
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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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J.O. Hoberg & B.L. Stocker. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 193 236 .
Veerababurao Kavala & Bhisma�K. Patel. (2005) Reinvestigation of the Mechanism ofgem-Diacylation: Chemoselective Conversion of Aldehydes to Variousgem-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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Rina Ghosh, Swarupananda Maiti, Arijit Chakraborty & Rajkumar Halder. (2004) Indium triflate: a reusable catalyst for expeditious chemoselective conversion of aldehydes to acylals. Journal of Molecular Catalysis A: Chemical 215:1-2, pages 49-53.
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Lingjun Li, Xinying Zhang, Guisheng Zhang & Guirong Qu. (2019) Efficient and Chemoselective Deprotection of 1,1-Diacetates Using Fe 2 (SO 4 ) 3 · x H 2 O as a Heterogeneous Catalyst . Journal of Chemical Research 2004:1, pages 39-40.
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Gustavo P. Romanelli, Horacio J. Thomas, Graciela T. Baronetti & Juan C. Autino. (2003) Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a Wells–Dawson acid (H6P2W18O62·24H2O). Tetrahedron Letters 44:6, pages 1301-1303.
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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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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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Massimo Curini, Francesco Epifano, Maria Carla Marcotullio, Ornelio Rosati & Morena Nocchetti. (2002) Preparation and deprotection of 1,1-diacetates (acylals) using zirconium sulfophenyl phosphonate as catalyst. Tetrahedron Letters 43:15, pages 2709-2711.
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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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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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Alan C. Spivey & Steven J. Woodhead. (1998) Chapter 2. Synthetic methods . Part (v) Protecting groups. Annual Reports Section "B" (Organic Chemistry) 94, pages 77.
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T.‐S. JIN, Y.‐R. MA, Z.‐H. ZHANG & T.‐S. LI. (2010) ChemInform Abstract: An Efficient and Facile Procedure for the Deprotection of 1,1‐ Diacetates Catalyzed by Expansive Graphite.. ChemInform 28:50.
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