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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 12
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Original Articles

Zinc Chloride Catalyzed Silylation of Alcohols and Phenols by Hexamethyldisilazane. A Highly Chemoselective Reaction

H. Firouzabadi Chemistry Department, College of Sciences, Shiraz University, Shiraz, Iram
&
B. Karimi Chemistry Department, College of Sciences, Shiraz University, Shiraz, Iram
Pages 1633-1641 | Received 23 Dec 1992, Published online: 23 Sep 2006

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Behzad Zeynizadeh & Serve Sorkhabi. (2018) Fast and efficient method for Silylation of alcohols and phenols with HMDS in the presence of bis-thiourea complexes of cobalt, nickel, copper and zinc chlorides. Phosphorus, Sulfur, and Silicon and the Related Elements 193:3, pages 127-135.
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Hossein Ghafuri, Fatemeh Paravand & Afsaneh Rashidizadeh. (2017) Nano Fe3O4@ZrO2/SO42−: A highly efficient catalyst for the protection and deprotection of hydroxyl groups using HMDS under solvent-free condition. Phosphorus, Sulfur, and Silicon and the Related Elements 192:1, pages 129-135.
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Boningari Thirupathi, AvvariN. Prasad, Rapelli Srinivas & BenjaramM. Reddy. (2011) Sulfated Zirconia: An Efficient Catalyst for Solvent-Free Synthesis of Silyl Ethers Under Mild Conditions. Synthetic Communications 41:14, pages 2064-2072.
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Batool Akhlaghinia. (2009) Novel and Highly Efficient Protection of Aliphatic Alcohols and Phenols with Hexamethyldisilazane in the Presence of La(NO3)3·6 H2O. Phosphorus, Sulfur, and Silicon and the Related Elements 184:10, pages 2530-2535.
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HosseinA. Oskooie, MajidM. Heravi, MaryamH. Tehrani, FarahnazK. Behbahani & OmidM. Heravi. (2009) Trimethylsilylation of Alcohols and Phenols, and Direct Acetylation of Silyl Ethers Catalyzed by Fe(ClO4)3.6H2O. Phosphorus, Sulfur, and Silicon and the Related Elements 184:7, pages 1729-1737.
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Hamid Reza Shaterian, Razieh Doostmohammadi, Majid Ghashang & Mashaallah Rahmani. (2008) A Mild, Simple, Efficient, and Selective Protection of Hydroxyl Groups Using Silica-Supported Sodium Hydrogen Sulfate as a Heterogeneous Catalyst. Phosphorus, Sulfur, and Silicon and the Related Elements 183:12, pages 3127-3135.
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Hamid Reza Shaterian, Fahimeh Khorami, Azita Amirzadeh & Majid Ghashang. (2008) Alumina Perchloric Acid (Al O -HClO ) as an Efficient Heterogeneous Catalyst for Modified Preparation of Trimethylsilyl Ethers. Phosphorus, Sulfur, and Silicon and the Related Elements 183:11, pages 2865-2874.
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Hamid Reza Shaterian, Fahimeh Khorami, Azita Amirzadeh, Majid Ghashang & Asghar Hosseinian. (2008) Alumina Sulfuric Acid as an Efficient and Recyclable Heterogeneous Catalyst for the O-Silylation of Alcohols, Phenols, and Oximes. Phosphorus, Sulfur, and Silicon and the Related Elements 183:10, pages 2584-2595.
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Amin Rostami, Ardeshir Khazaei, Marjan Mahboubifar & Sadegh Rahmati. (2008) CONVENIENT TREMETHYLSILYLATION OF HYDROXY GROUPS WITH HEXAMETHYLDISILAZANE UNDER SOLVENT-FREE CONDITIONS. Organic Preparations and Procedures International 40:3, pages 303-306.
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Hassan Ghasemnejad-Bosra, Mahmood Tajbakhsh, Farhad Ramzanian-Lehmali, Majid Shabani-Mahali & MohammadA. Khalilzadeh. (2008) A Mild and Efficient Method for Oxidative Deprotection of Trimethylsilyl Ethers to the Corresponding Carbonyl Compounds Using [PhCH2NMe2Ph]2S2O8 . Phosphorus, Sulfur, and Silicon and the Related Elements 183:6, pages 1496-1500.
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Mahmoud Tajbakhsh, Heshmatollah Alinezhad & Azade Geran Urimi. (2008) Oxidative Deprotection of Trimethylsilyl Ethers to the Corresponding Carbonyl Compounds Using Cetyltrimethylammonium Peroxodisulfate. Phosphorus, Sulfur, and Silicon and the Related Elements 183:6, pages 1447-1454.
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Arash Shokrollahi, Abbas Zali & Hamid Reza Pouretedal. (2008) High‐Efficiency Conversion of Trimethylsilyl Ethers to Their Corresponding Ethers using Carbon‐Based Solid Acid as a New Catalyst in Heterogeneous Mixtures. Synthetic Communications 38:3, pages 371-375.
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Hamid Reza Shaterian & Majid Ghashang. (2007) A Highly Efficient Method for the Silylation of Alcohols, Phenols, and Naphthols Using HMDS in the Presence of Zinc Oxide (ZnO) as Economical Heterogeneous Catalyst. Phosphorus, Sulfur, and Silicon and the Related Elements 183:1, pages 194-204.
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Hossein Ghafuri, Bagher Eftekhari-Sis & MohammedM. Hashemi. (2007) Silica Sulfuric Acid as a Reusable Catalyst for Efficient and Simple Silylation of Hydroxyl Groups Using Hexamethyldisilazane (HMDS). Phosphorus, Sulfur, and Silicon and the Related Elements 182:7, pages 1645-1651.
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Batool Akhlaghinia. (2007) A New and Efficient Method for the Protection of Alcohols and Phenols by Using Hexamethyldisilazane in the Presence of Anhydrous Ferric Chloride under Mild Reaction Conditions. Phosphorus, Sulfur, and Silicon and the Related Elements 182:3, pages 687-694.
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Vrushali H. Jadhav, K. S. Ajish Kumar, Vinod D. Chaudhari & Dilip D. Dhavale. (2007) Facile Method for Trimethylsilylation of Alcohols using Hexamethyldisilazane and Ammonium Thiocyanate under Neutral Conditions. Synthetic Communications 37:8, pages 1363-1370.
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Tong‐Shou Jin, Ruo‐Fei Tian, Li‐Bin Liu, Ying Zhao & Tong‐Shuang Li. (2006) Silica Sulfate, an Efficient Catalyst for the Trimethylsilylation of Alcohols. Synthetic Communications 36:13, pages 1823-1828.
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Farhad Shirini, Majid Esm‐Hosseini & Zoha Hejazi. (2005) (NO3)3CeBrO3: Solvent‐Free Oxidation of Alcohols and Deprotection and Oxidative Deprotection of Trimethylsilyl Ethers. Synthetic Communications 35:22, pages 2913-2919.
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Mohammad Ali Zolfigol, Iraj Mohammadpoor-Baltork, Davood Habibi, BiBi Fatemeh Mirjalili & Abdolhamid Bamoniri. (2004) THE USE OF NAFION-H® AS AN EFFICIENT CATALYST FOR THE DEPROTECTION OF TRIMETHYLSILYL ETHERS TO THEIR CORRESPONDING ALCOHOLS UNDER MILD AND HETEROGENEOUS CONDITIONS. Phosphorus, Sulfur, and Silicon and the Related Elements 179:11, pages 2189-2193.
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Batool Akhlaghinia, Mozafar Asadi, Elham Safaee & Mozhgan Heydarpoor. (2004) HEXAMETHYLDISILAZANE IN THE PRESENCE OF N,N′,N″,N‴-TETRAMETHYLTETRA-2,3-PYRIDINOPORPHYRAZINATO COPPER (II) IS A NEW, MILD AND HIGHLY EFFICIENT REAGENT FOR SILYLATION OF ALCOHOLS AND PHENOLS. Phosphorus, Sulfur, and Silicon and the Related Elements 179:10, pages 2099-2104.
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Habib Firouzabadi, Hassan Hassani & Mostafa Gholizadeh. (2004) IMMEDIATE AND HIGH YIELDING SOLVENT-FREE OXIDATION OF SILYL AND PYRANYL ETHERS TO THEIR CORRESPOUNDING CARBONYL COMPOUNDS WITH ZINC DICHROMATE TRIHYDRATE (ZnCr2O7·3H2O). Phosphorus, Sulfur, and Silicon and the Related Elements 179:7, pages 1417-1422.
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M. M. Mojtahedi, M. R. Saidi, M. Bolourtchian & M. M. Heravi. (2002) Silylation of Hydroxy Groups with HMDS Under Microwave Irradiation and Solvent-Free Conditions. Phosphorus, Sulfur, and Silicon and the Related Elements 177:2, pages 289-292.
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I. Mohammadpoor-Baltork, A. R. Hajipour & M. Aghajari. (2002) SELECTIVE AND EFFICIENT OXIDATIVE DEPROTECTION OF TRIMETHYLSILYL AND TETRAHYDROPYRANYL ETHERS, ETHYLENE ACETALS AND KETALS WITH n-BUTYLTRIPHENYLPHOSPHONIUM PEROXODISULFATE (Bu PPh3)2S2O8 . Synthetic Communications 32:9, pages 1311-1317.
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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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Ahmad Shaabani & Ali-Reza Karimi. (2001) OXIDATION DEPROTECTION OF TRIMETHYLSILYL ETHERS TO CARBONYL COMPOUNDS BY NaBrO3-NH4Cl REAGENT IN AQUEOUS ACETONITRILE. Synthetic Communications 31:5, pages 759-765.
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Habib Firouzabadi, Shahrad Etemadi, Babak Karimi & Ali Asghar Jarrahpour. (1999) A STUDY OF OXIDATIVE DEPROTECTION OF TRIMETHYLSILYL (TMS) AND TERT-BUTYLDIMEHYLSILYL (TBDMS) ETHERS OF ALCOHOLS WITH POTASSIUM PERMANGANATE (KMnO4) AND BARIUM MANGANATE (BAMnO4) IN THE PRESENCE OF LEWIS ACIDS IN DRY ORGANIC SOLVENTS. Phosphorus, Sulfur, and Silicon and the Related Elements 152:1, pages 141-151.
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Zhan-Hui Zhang, Tong-Shuang Li, Feng Yang & Cheng-Guang Fu. (1998) Montmorillonite Clay Catalysis XI1: Protection and Deprotection of Hydroxyl Group by Formation and Cleavage of Trimethylsilyl Ethers Catalysed by Montmorillonite K-10. Synthetic Communications 28:16, pages 3105-3114.
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H. Firouzabadi, A.R. Sardarian, Z. Khayat, B. Karimi & S. Tangestaninejad. (1997) Nitrogen Ligand Complexes of Metal Chlorides as Effective Catalysts for the Highly Regio- and Chemoselective Silylation of Hydroxyl Groups with Hexamethyldisilazane (HMDS) at Room Temperature. Synthetic Communications 27:15, pages 2709-2719.
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H. Firouzabadi & G.R. Afsharifar. (1996) Facile Deprotection of Trimethylsilyl Ethers With Modified Borohydride Agents; 1-Benzyl-4-AZA-1-Azoniabicyclo[2.2.2]Octane Tetrahydroborate (Baaotb)1 Versus Tetrabutylammonium Tetrahydroborate(TBATB). Synthetic Communications 26:6, pages 1065-1073.
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H. Firouzabadi & F. Shiriny. (1996) Bis[Trinitrato Cerium(IV)] Chromate; [(NO3)3Ce]2 CrO4 vs Trinitrato Cerium(IV) Chromate Dihydrate; [(NO3)3Ce] CrO4.2H2O in the oxidation of trimethylsilyl ethers. Synthetic Communications 26:4, pages 649-655.
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H. Firouzabadi & I. Mohammadpoor-Baltork. (1994) Lewis Acid Promoted Reactions. (IV.)1a,b Oxidation Deprotection of Trimethylsilyl Ethers with Silver and Sodium Bromates; AgBrO3, NaBrO3 . Synthetic Communications 24:8, pages 1065-1077.
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Mahmood Tajbakhsh, Iraj Mohammadpoor-Baltork & Farhad Ramzanian-Lehmali. (2019) Benzyltriphenylphosphonium Peroxodisulfate: A Mild and Inexpensive Reagent for Selective Oxidative Deprotection of Trimethylsilyl and Tetrahydropyranyl Ethers, Ethylene Acetals and Ketals under Non-Aqueous and Aprotic Conditions. Journal of Chemical Research 2001:5, pages 185-187.
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