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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 21
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Original Articles

Synthesis of Thiiranes From Oxiranes Under Mild and Nonaqueous Conditions Using Polymer Supported Thiocyanate

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Pages 3953-3958 | Received 25 Apr 1996, Published online: 23 Aug 2006

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Read on this site (28)

Ronak Eisavi & Behzad Zeynizadeh. (2016) A green protocol for rapid and efficient conversion of epoxides to thiiranes using alumina immobilized thiourea at solvent-free conditions. Phosphorus, Sulfur, and Silicon and the Related Elements 191:1, pages 65-69.
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Mohammad Ali Karimi Zarchi & Asmaosadat Tabatabaei Bafghi. (2015) Synthesis of alkyl thiocyanates from alcohols using a polymer-supported thiocyanate ion promoted by cyanuric chloride/dimethylformamide. Journal of Sulfur Chemistry 36:4, pages 403-412.
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Mohammad Ali Karimi Zarchi & Nahid Ebrahimi. (2012) An Efficient and Simple Method for Diazotization-Thiocyanation of Aryl Amine using Cross-Linked Poly (4-Vinylpyridine) Supported Thiocyanate Ion. Phosphorus, Sulfur, and Silicon and the Related Elements 187:10, pages 1226-1235.
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Batool Akhlaghinia, Mohammad Rahimizadeh, Hosein Eshghi, Sara Zhaleh & Soodabeh Rezazadeh. (2012) Green synthesis of thiiranes from oxiranes under solvent- and catalyst-free conditions. Journal of Sulfur Chemistry 33:3, pages 351-361.
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Behzad Zeynizadeh, Mohammad Mehdi Baradarani & Ronak Eisavi. (2011) A Practical and Eco-Friendly Method for Conversion of Epoxides to Thiiranes with Immobilized Thiourea on CaCO3 . Phosphorus, Sulfur, and Silicon and the Related Elements 186:11, pages 2208-2215.
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Ronak Eisavi, Behzad Zeynizadeh & Mohammad Mehdi Baradarani. (2011) Zeolite Molecular Sieve 4Å: A Reusable Catalyst for Fast and Efficient Conversion of Epoxides to Thiiranes with Thiourea. Phosphorus, Sulfur, and Silicon and the Related Elements 186:9, pages 1902-1909.
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Liqiang Wu, Limin Yang, Lizhen Fang, Chunguang Yang & Fulin Yan. (2010) Silica Chloride–Catalyzed Synthesis of Thiiranes from Oxiranes Under Solvent-Free Conditions. Phosphorus, Sulfur, and Silicon and the Related Elements 185:10, pages 2159-2164.
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Behzad Zeynizadeh & Samal Yeghaneh. (2009) A Green Protocol for Solvent-Free Conversion of Epoxides to Thiiranes with Dowex-50WX8–Supported Thiourea. Phosphorus, Sulfur, and Silicon and the Related Elements 184:2, pages 362-368.
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Behzad Zeynizadeh & Samal Yeghaneh. (2008) Solvent-Free Conversion of Epoxides to Thiiranes by Thiourea/NH4Cl System. Phosphorus, Sulfur, and Silicon and the Related Elements 183:9, pages 2280-2286.
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Nasser Iranpoor, Habib Firouzabadi & Abbas Ali Jafari. (2005) A Green Protocol for the Easy Synthesis of Thiiranes from Epoxides Using Thiourea/Silica Gel in the Absence of Solvent. Phosphorus, Sulfur, and Silicon and the Related Elements 180:8, pages 1809-1814.
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B. Tamami & K. Parvanak Borujeny. (2004) Synthesis of Thiiranes from Oxiranes Using Cross‐Linked Polystyrene Supported Aluminium Chloride as a Catalyst. Synthetic Communications 34:1, pages 65-70.
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Hashem Sharghi & Alireza Hassani Nejad. (2004) DICHLORO (5,10,15,20-TETRAPHENYLPORPHYRIN) PHOSPHORUS(V) CHLORIDE AS A NEW CATALYST FOR CONVERSION OF 1,2-EPOXYETHANES TO 2-HYDROXYETHYL THIOCYANATES WITH AMMONIUM THIOCYANATE. Phosphorus, Sulfur, and Silicon and the Related Elements 179:11, pages 2297-2305.
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Ali Reza Kiasat, Foad Kazemi & Mehdi Fallah Mehr Jardi. (2004) SOLVENT-FREE CONVERSION OF OXIRANES TO THIIRANES WITH THIOUREA. Phosphorus, Sulfur, and Silicon and the Related Elements 179:9, pages 1841-1844.
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Bahram Yadollahi, Shahram Tangestaninejad & Mohammad Hossein Habibi. (2004) Titanium Dioxide as a Mild and Efficient Catalyst for Conversion of Epoxides to Thiiranes. Synthetic Communications 34:15, pages 2823-2827.
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Hashem Sharghi & Mohammad Ali Nasseri. (2003) 2-Phenyl-2-(2-pyridyl)imidazolidine (PPI) as New Catalyst in the Efficient, Mild, and Regioselective Conversion of Epoxides to Thiocyanohydrines with Ammonium Thiocyanate. Phosphorus, Sulfur, and Silicon and the Related Elements 178:6, pages 1353-1359.
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Foad Kazemi & Ali Reza Kiasat. (2003) Facile Conversion of Epoxides to Thiiranes with Ammonium Thiocyanate Catalyzed with Oxalic Acid. Phosphorus, Sulfur, and Silicon and the Related Elements 178:6, pages 1333-1337.
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F. Kazemi, A. R. Kiasat & S. Ebrahimi. (2003) LiBF4: A Mild and Efficient Catalyst for Conversion of Oxiranes to Thiiranes with Thiourea. Synthetic Communications 33:4, pages 595-600.
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Foad Kazemi, Ali Reza Kiasat & Shahriar Ebrahimi. (2001) Efficient Conversion of Oxiranes to Thiiranes with Thiourea Catalyzed with Ruthenium Trichloride and Alumina. Phosphorus, Sulfur, and Silicon and the Related Elements 176:1, pages 135-140.
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B. Tamami & A.R. Kiasat. (2000) A Convenient Conversion of Aldoximes to Nitriles Using A Polymer Supported System. Synthetic Communications 30:2, pages 235-242.
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N. Iranpoor, B. Tammi & M. Shekarriz. (1999) Conversion of Epoxides to Thiiranes with Thiourea or Ammonium Thiocyanate Catalyzed with Poly(4-Vinyl Pyridine)-Ce(OTf)4 . Synthetic Communications 29:19, pages 3313-3321.
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Nasser Iranpoor & Gholam Ali Kohmareh. (1999) DDQ CATALYSES THE CONVERSION OF EPOXIDES TO ß-HYDROXY THIOCYANATES WITH NH4SCN. Phosphorus, Sulfur, and Silicon and the Related Elements 152:1, pages 135-139.
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S. Tangestaninejad & V. Mirkhani. (1999) Efficient Conversion of Epoxides to Thiiranes with Thiourea Catalyzed by Tin(IV) Porphyrin. Synthetic Communications 29:12, pages 2079-2083.
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I. Mohammadpoor-Baltork & H. Aliyan. (1998) Bismuth(III) Chloride; A Mild and Efficient Catalyst for Synthesis of Thiiranes from Oxiranes. Synthetic Communications 28:21, pages 3943-3947.
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Somayeh Behrouz, Mohammad Navid Soltani Rad & Mohammad Amin Piltan. (2018) Ultrasound promoted rapid and green synthesis of thiiranes from epoxides in water catalyzed by chitosan-silica sulfate nano hybrid (CSSNH) as a green, novel and highly proficient heterogeneous nano catalyst. Ultrasonics Sonochemistry 40, pages 517-526.
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S. Abdolmanaf Taghavi, Majid Moghadam, Iraj Mohammadpoor-Baltork, Shahram Tangestaninejad, Valiollah Mirkhani, Ahmad Reza Khosropour & Venus Ahmadi. (2011) Investigation of the catalytic activity of an electron-deficient vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for ring-opening of epoxides. Polyhedron 30:13, pages 2244-2252.
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Liqiang Wu, Yongxue Wang, Fulin Yan & Chunguang Yang. (2010) Facile Conversion of Epoxides to Thiiranes with Ammonium Thiocyanate Catalyzed with Etidronic Acid. Bulletin of the Korean Chemical Society 31:5, pages 1419-1420.
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Ali Reza Kiasat, Arash Mouradzadegun, Somayeh Elahi & Mehdi Fallah-Mehrjardi. (2010) Al(HSO4)3/silica gel as a novel catalytic system for the ring opening of epoxides with thiocyanate anion under solvent-free conditions. Chinese Chemical Letters 21:2, pages 146-150.
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Ali Reza Kiasat, Roya Mirzajani, Haji Shalbaf & Tahereh Tabatabaei. (2009) Nuclephilic ring opening of epoxides promoted by multi-site phase-transfer catalyst: An efficient and eco-friendly route to synthesis of β-hydroxy-thiocyanate. Chinese Chemical Letters 20:9, pages 1025-1029.
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Ali Reza Kiasat & Mehdi Fallah‐Mehrjardi. (2013) Dowex as Reusable Acidic Polymeric Catalyst in the Efficient and Regioselective Conversion of Epoxides into β‐Hydroxy Thiocyanates under Solvent Free Conditions. Journal of the Chinese Chemical Society 55:5, pages 1119-1124.
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Ana Bellomo & David Gonzalez. (2007) Diasterodivergent synthesis of optically pure vinyl episulfides and β-hydroxy thiocyanates from a bacterial metabolite. Tetrahedron Letters 48:17, pages 3047-3051.
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K. Surendra, N. Srilakshmi Krishnaveni & K. Rama Rao. (2004) A new and efficient method for the synthesis of thiiranes from oxirane–β-cyclodextrin complexes and thiourea in water. Tetrahedron Letters 45:34, pages 6523-6526.
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N. Srilakshmi Krishnaveni, K. Surendra, M. Somi Reddy, Y. V. D. Nageswar & K. Rama Rao. (2004) Synthesis of Thiiranes from Oxiranes in the Presence of β‐Cyclodextrin in Water. Advanced Synthesis & Catalysis 346:4, pages 395-397.
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Bahman Tamami & Majid Kolahdoozan. (2004) Synthesis of thiiranes from oxiranes in water using polymeric cosolvents. Tetrahedron Letters 45:7, pages 1535-1537.
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J.S. Yadav, B.V.S. Reddy & Ch.Srinivas Reddy. (2004) Selectfluor™: a novel and efficient reagent for the synthesis of β-hydroxy thiocyanates. Tetrahedron Letters 45:6, pages 1291-1293.
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Babak Kaboudin & Hamid Norouzi. (2004) A new, efficient, and simple method for the synthesis of thiiranes from epoxides under solvent-free conditions. Tetrahedron Letters 45:6, pages 1283-1285.
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Hashem Sharghi, Alireza Hassani Nejad & Mohammad Ali Nasseri. (2004) Metalloporphyrins as new catalysts in the mild, efficient and regioselective conversion of epoxides to β-hydroxy thiocyanates with NH 4 SCN . New J. Chem. 28:8, pages 946-951.
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Hashem Sharghi, Mohammad Ali Nasseri & Alireza Hassani Nejad. (2003) Efficient synthesis of β-hydroxy thiocyanates from epoxides and ammonium thiocyanates using tetraarylporphyrins as new catalysts. Journal of Molecular Catalysis A: Chemical 206:1-2, pages 53-57.
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F. Kazemi & A.R. Kiasat. (2019) Efficient Conversion of Epoxides to Episulfides with Thiourea Catalysed with Cerium (IV). Journal of Chemical Research 2003:5, pages 290-291.
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J. S. Yadav, B. V. S. Reddy, Ch. Srinivas Reddy & K. Rajasekhar. (2003) [Bmim]PF 6 :  A Novel and Recyclable Ionic Liquid for Conversion of Oxiranes to Thiiranes in Aqueous Media . The Journal of Organic Chemistry 68:6, pages 2525-2527.
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Hashem Sharghi & Mohammad Ali Nasseri. (2003) Schiff-Base Metal(II) Complexes as New Catalysts in the Efficient, Mild and Regioselective Conversion of 1,2-Epoxyethanes to 2-Hydroxyethyl Thiocyanates with Ammonium Thiocyanate. Bulletin of the Chemical Society of Japan 76:1, pages 137-142.
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Bahman Tamami & Hossein Mahdavi. (2002) Synthesis of thiocyanohydrins from epoxides using quaternized amino functionalized cross-linked polyacrylamide as a new solid–liquid phase-transfer catalyst. Tetrahedron Letters 43:35, pages 6225-6228.
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Georges Gelbard. 2002. Handbook of Green Chemistry and Technology. Handbook of Green Chemistry and Technology 150 187 .
F. Kazemi, A.R. Kiasat & S. Ebrahimi. (2019) Efficient Conversion of Oxiranes to Thiiranes with Ammonium Thiocyanate Catalysed with LiBF 4 . Journal of Chemical Research 2002:4, pages 176-177.
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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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Hashem Sharghi, Mohammad Ali Nasseri & Khodabakhsh Niknam. (2001) Phenol-Containing Macrocyclic Diamides as New Catalysts in the Highly Regioselective Conversion of Epoxides to β-Hydroxy Thiocyanates. The Journal of Organic Chemistry 66:22, pages 7287-7293.
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Iraj Mohammadpoor-Baltork & Hamid Aliyan. (2019) Montmorillonite K-10: A Mild, Inexpensive and Convenient Catalyst for Synthesis of Thiiranes from Oxiranes under Non-Aqueous Conditions. Journal of Chemical Research 2000:3, pages 122-123.
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Agnes Olszewski-Ortar, Philippe Gros & Yves Fort. (1997) Selective ring-opening of ω-epoxyalkyl (meth)acrylates. An efficient access to bifunctional monomers. Tetrahedron Letters 38:50, pages 8699-8702.
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