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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 6
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Original Articles

A RAPID, SELECTIVE, AND EFFICIENT METHOD FOR DEPROTECTION OF SILYL ETHERS CATALYZED BY BISMUTH(III) SALTS

H. Firouzabadi Department of Chemistry, Shiraz University, Shiraz, 71454, Iran
,
I. Mohammadpoor-Baltork Department of Chemistry, Isfahan University, Isfahan, 81744, Iran
&
S. Kolagar Department of Chemistry, Isfahan University, Isfahan, 81744, Iran
Pages 905-909 | Received 24 Apr 2000, Published online: 09 Nov 2006

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Ch. Subramanyam, G. Madhava, S. K. Thaslim Basha, S. Rasheed, A. Uday Sankar & C. Naga Raju. (2015) Bismuth(III) Chloride Mediated Michaelis–Arbuzov Reaction: A Facile Synthesis of Substituted Arylphosphonates/Phosphinates and Bioactivity Evaluation. Phosphorus, Sulfur, and Silicon and the Related Elements 190:11, pages 1948-1957.
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Junmin Zhang & Songlin Zhang. (2007) Bismuth(III) Chloride–Promoted Efficient Synthesis of Perimidine Derivatives under Ambient Conditions. Synthetic Communications 37:15, pages 2615-2624.
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Davood Azarifar & Behrooz Maleki. (2005) Microwave‐Assisted Aromatization of 1,3,5‐Trisubstituted 2‐Pyrazolines by Bi(NO3)3 · 5H2O, as a Novel and Convenient Oxidizing Agent. Synthetic Communications 35:19, pages 2581-2585.
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Nasser Iranpoor, Habib Firouzabadi & Ali Reza Pourali. (2005) Selective Oxidation of Benzylic Alcohols and Ethers and Oxidative Cleavage of Benzylic Tetrahydropyranyl and Trimethylsilyl Ethers to Their Carbonyl Compounds by Dinitrogen Tetroxide–Impregnated Activated Charcoal (N2O4/Charcoal). Synthetic Communications 35:11, pages 1527-1533.
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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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Shikha Rani, J. Lokesh Babu & Yashwant D. Vankar. (2003) Selective Deprotection of -Butyldimethylsilyl Ethers Using Nafion-H®/Sodium Iodide (or Bromodimethylsulfonium Bromide) in Methanol. Synthetic Communications 33:23, pages 4043-4052.
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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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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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Georgijs Stakanovs, Anastasija Blazevica, Sergey Belyakov, Dace Rasina & Aigars Jirgensons. (2023) Semisynthesis of Linariophyllenes A–C and Rumphellolide H, Structure Revisions and Proposed Biosynthesis Pathways. Journal of Natural Products 86:10, pages 2368-2378.
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Guangying Lu, Di Wang, Jiangmeng Ren, Yanxiong Ke & Bu-Bing Zeng. (2019) Catalytic removal of tert-butyldimethylsilyl (TBS) ether by PVP-I. Tetrahedron Letters 60:39, pages 150831.
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Vishvanath D. Patil, Nagesh R. Sutar, Ketan P. Patil & Prathamesh Giddh. (2016) BiCl3 – an eco-friendly catalyst for an efficient synthesis of benzoxazoles at room temperature. Chemistry of Heterocyclic Compounds 51:11-12, pages 1019-1022.
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. 2014. Greene's Protective Groups in Organic Synthesis. Greene's Protective Groups in Organic Synthesis 17 471 .
Malik Hellal, Florian C. Falk, Eléna Wolf, Marian Dryzhakov & Joseph Moran. (2014) Breaking the dichotomy of reactivity vs. chemoselectivity in catalytic S N 1 reactions of alcohols . Org. Biomol. Chem. 12:31, pages 5990-5994.
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Reza Sandaroos, Mohammad Taghi Goldani & Saman Damavandi. (2012) One-pot synthesis of acenaphtho[1,2- b ]pyrroles in the presence of supported ionic liquid catalyst . hc 18:3, pages 157-160.
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Atul Chaskar, Latika Patil, Kiran Phatangare, Vikas Padalkar & Santosh Takale. (2011) Bismuth (III) Salts Promoted and Ionic Liquid Assisted an Efficient and Environmentally Benign One-Pot Synthesis of 1,5-Benzodiazepine Derivatives. ISRN Organic Chemistry 2011, pages 1-4.
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Bahram Yadollahi, Valiollah Mirkhani, Shahram Tangestaninejad & Davud Karimian. (2011) Rapid and efficient protection of alcohols and phenols, and deprotection of trimethylsilyl ethers catalyzed by a cerium-containing polyoxometalate. Applied Organometallic Chemistry 25:2, pages 83-86.
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Thierry Ollevier, Etienne Nadeau & Valerie Desyroy. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Tangali R. Ravikumar Naik, Halehatty S. Bhojya Naik, Halehatty R. Prakasha Naik & P. J. Bindu. (2008) Three-Component One-Pot Synthesis of Novel Benzo[ ]1,8-naphthyridines Catalyzed by Bismuth(III) Chloride . Research Letters in Organic Chemistry 2008, pages 1-4.
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Rajesh Sunasee & Derrick L. J. Clive. (2008) A Route to 1,4-Disubstituted Aromatics and Its Application to the Synthesis of the Antibiotic Culpin. The Journal of Organic Chemistry 73:20, pages 8016-8020.
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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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Tangali R. Ravikumar Naik & Halehatty S. Bhojya Naik. (2008) An efficient Bi(NO3)3 · 5H2O catalyzed multi component one-pot synthesis of novel Naphthyridines. Molecular Diversity 12:2, pages 139-142.
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Iraj Mohammadpoor-Baltork, Ahmad R. Khosropour & Seyedeh F. Hojati. (2007) Mild and Efficient Synthesis of Benzoxazoles, Benzothiazoles, Benzimidazoles, and Oxazolo[4,5-b]pyridines Catalyzed by Bi(III) Salts Under Solvent-Free Conditions. Monatshefte für Chemie - Chemical Monthly 138:7, pages 663-667.
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Mohammad A. Zolfigol, Farhad Shirini, Iraj Mohammadpoor-Baltork, Arash Gh. Choghamarani, Maryam Hajjami & Abdol M. Sedaghat. (2005) Silica chromate as an oxidising agent for the chemoselective oxidation of alcohols and the oxidative deprotection of trimethylsilyl ethers. Mendeleev Communications 15:3, pages 113-116.
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R. David Crouch. (2004) Selective monodeprotection of bis-silyl ethers. Tetrahedron 60:28, pages 5833-5871.
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Hafida Gaspard‐Iloughmane & Christophe Le Roux. (2004) Bismuth( III ) Triflate in Organic Synthesis . European Journal of Organic Chemistry 2004:12, pages 2517-2532.
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R.David Crouch, Candice A. Romany, Anna C. Kreshock, Karina A. Menconi & Jennifer L. Zile. (2004) BiOClO 4 -mediated deprotection of silyl ethers. Tetrahedron Letters 45:6, pages 1279-1281.
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S. Venkat Reddy, R. Jagadeeshwar Rao, U. Sampath Kumar & J. Madhusudana Rao. (2003) Highly Efficient and Convenient Deprotection of Methoxymethyl Ethers and Esters Using Bismuth Triflate in an Aqueous Medium. Chemistry Letters 32:11, pages 1038-1039.
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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 18 89 .
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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Alan C. Spivey & David Leese. (2002) 2  Synthetic methods : Part (iii) Protecting groups. Annu. Rep. Prog. Chem., Sect. B: Org. Chem. 98, pages 41-60.
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H. Firouzabadi, I. Mohammadpoor‐Baltork & S. Kolagar. (2010) ChemInform Abstract: A Rapid, Selective, and Efficient Method for Deprotection of Silyl Ethers Catalyzed by Bismuth(III) Salts.. ChemInform 32:36.
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