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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 5
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Original Articles

Synthesis of β-Trimethylsilyloxythioethers and β-Hydroxythioethers by the Reaction of Epoxides with Aryl- and Alkylthiotrimethylsilanes

Yvan Guindon Merck Frosst Laboratories, P.O. Box 1005, Pointe-Claire/Dorval, Québec, Canada, H9R 4P8
,
Robert N. Young Merck Frosst Laboratories, P.O. Box 1005, Pointe-Claire/Dorval, Québec, Canada, H9R 4P8
&
Richard Frenette Merck Frosst Laboratories, P.O. Box 1005, Pointe-Claire/Dorval, Québec, Canada, H9R 4P8
Pages 391-398 | Published online: 05 Dec 2006

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Daniel J. Meininger, Zieph Kasrawi, Hadi D. Arman & Zachary J. Tonzetich. (2016) Synthesis of tetraphenylporphyrinate manganese(III) siloxides by silyl group transfer from silanethiols. Journal of Coordination Chemistry 69:11-13, pages 1970-1978.
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Antonella Capperucci & Damiano Tanini. (2015) Silicon-Assisted Synthesis and Functionalization of Sulfurated and Selenated Compounds. Phosphorus, Sulfur, and Silicon and the Related Elements 190:8, pages 1320-1338.
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M. Shailaja, A. Manjula & B. Vittal Rao. (2010) (Bromodimethyl)sulfonium Bromide–Mediated Thiolysis of Epoxides: An Easy Access to β-Hydroxy Sulfides and Benzoxathiepinones in Solvent-Free Conditions. Synthetic Communications 40:24, pages 3629-3639.
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S. Munavalli, D.K. Rohrbaugh, R.A. Mackay, F.R. Longo & H.D. Durst. (2005) Reaction of Epoxides with (Alkylthio)methyl Chloride. Phosphorus, Sulfur, and Silicon and the Related Elements 180:12, pages 2689-2700.
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H. Mahdavi & B. Tamami. (2005) Synthesis of β -Dihydroxysulfides by Cleavage of Epoxides Using Quaternized Amino-Functionalized Cross-Linked Polyacrylamide as a New Polymeric Phase Transfer Catalyst. Phosphorus, Sulfur, and Silicon and the Related Elements 180:8, pages 1929-1936.
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S. Munavalli, ROBERT SCHLUETER, D.K. Rohrbaugh, R.L. Longo, R.A. Mackay & H.D. Durst. (2005) Unusual Reaction of Epoxynorbornane with Trifluoromethylsulfenyl Chloride. Phosphorus, Sulfur, and Silicon and the Related Elements 180:2, pages 309-320.
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S. Munavalli, D.K. Rohrbaugh & H.D. Durst. (2004) TRIFLUOROMETHYLTHIOCOPPER CATALYZED OXIRANE RING OPENING. Phosphorus, Sulfur, and Silicon and the Related Elements 179:8, pages 1657-1671.
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Alessandro Degl'innocenti & Antonella Capperucci. (1998) Organosilanes in Sulfur Chemistry: Silicon Mediated Synthesis and Reactivity of Sulfur-Containing Molecules. Sulfur reports 20:3, pages 279-395.
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Articles from other publishers (23)

C. Wade Downey, Sarah E. Covington, Derek C. Obenschain, Evan Halliday, James T. Rague & Danielle N. Confair. (2014) Silyl trifluoromethanesulfonate-activated para-methoxybenzyl methyl ether as an alkylating agent for thiols and aryl ketones. Tetrahedron Letters 55:37, pages 5213-5215.
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Changzhen Sun, Yuebao Zhang, Peihong Xiao, Hongze Li, Xianwei Sun & Zhenlei Song. (2014) Intramolecular [1,4]- S - to O -Silyl Migration: A Useful Strategy for Synthesizing Z -Silyl Enol Ethers with Diverse Thioether Linkages . Organic Letters 16:3, pages 984-987.
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Xianwei Sun, Zhenlei Song, Hongze Li & Changzheng Sun. (2013) [1,4]‐S‐ to O‐Silyl Migration: Multicomponent Synthesis of α‐Thioketones through Chemoselective Transformation of Esters to Ketones with Organolithium Reagents. Chemistry – A European Journal 19:51, pages 17589-17594.
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Alexandre Walther, Delphine Josien-Lefebvre & Claude Le Drian. (2011) New very mild conditions for the opening of an epoxide assisted by a neighboring carbonyl group. Tetrahedron Letters 52:20, pages 2550-2553.
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Antonella Capperucci, Caterina Tiberi, Salvatore Pollicino & Alessandro Degl’Innocenti. (2009) Tetrabutylammonium phenoxide induced reaction of silyl nucleophiles. Tetrahedron Letters 50:23, pages 2808-2810.
Crossref
William C. Groutas, Larissa B. Krasnova & Andrei K. Yudin. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Antonella Capperucci, Alessandro Degl'Innocenti, Salvatore Pollicino, Miriam Acciai, Giulio Castagnoli, Irene Malesci & Caterina Tiberi. (2007) Thiosilanes in sulfur chemistry: A general approach to silyl thiaheterocycles and their use in stereoselective synthesis. Heteroatom Chemistry 18:5, pages 516-526.
Crossref
Alessandro Degl'Innocenti, Salvatore Pollicino & Antonella Capperucci. (2006) Synthesis and stereoselective functionalization of silylated heterocycles as a new class of formyl anion equivalents. Chemical Communications:47, pages 4881.
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Zbigniew Grobelny, Andrzej Stolarzewicz, Barbara Morejko-Bu?Adalbert Maercker. (2004) Study on the initiation step of vinyloxirane and 3-butenyloxirane polymerization by alkalide K?, K+(15-crown-5)2. European Polymer Journal 40:2, pages 409-414.
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Francesco Fringuelli, Ferdinando Pizzo, Simone Tortoioli & Luigi Vaccaro. (2003) Zn(II)-Catalyzed Thiolysis of Oxiranes in Water under Neutral Conditions. The Journal of Organic Chemistry 68:21, pages 8248-8251.
Crossref
Naduthambi Devan, Perali Ramu Sridhar, Kandikere Ramaiah Prabhu & Srinivasan Chandrasekaran. (2002) Tetrathiomolybdate Assisted Epoxide Ring Opening with Masked Thiolates and Selenoates:  Multistep Reactions in One Pot. The Journal of Organic Chemistry 67:26, pages 9417-9420.
Crossref
Glenn J. McGarvey. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Jeffrey A. McKinney. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
William C. Groutas. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
William C. Groutas. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
S Munavalli, D.K Rohrbaugh, D.I Rossman, L.R McMahon & H.D Durst. (1999) Trifluoromethylthiocopper-mediated oxirane ring opening. Journal of Organometallic Chemistry 587:2, pages 160-164.
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D. A. (‘Fred’) Armitage, Robert. J. P. Corriu, Tom C. Kendrick, Bhukan Parbhoo, T. Don Tilley, James W. White & J. Colin YoungD. A. (‘Fred’) Armitage. 1991. The Silicon–Heteroatom Bond (1991). The Silicon–Heteroatom Bond (1991) 213 232 .
Bruce Rickborn. 1991. Comprehensive Organic Synthesis. Comprehensive Organic Synthesis 733 775 .
J. Rokach, Y. Guindon, R.N. Young, J. Adams & J.G. Atkinson. 1988. Total Synthesis of Natural Products. Total Synthesis of Natural Products 141 273 .
Jacques Yves Gauthier, France Bourdon & Robert Norman Young. (1986) A mild and efficient synthesis of thiolesters from alcohols. Tetrahedron Letters 27:1, pages 15-18.
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M. Bartók & K. L. Láng. 1985. Chemistry of Heterocyclic Compounds. Chemistry of Heterocyclic Compounds 1 196 .
A.S. Rao, S.K. Paknikar & J.G. Kirtane. (1983) Recent advances in the preparation and synthetic applications of oxiranes. Tetrahedron 39:14, pages 2323-2367.
Crossref
Y. GUINDON, R. N. YOUNG & R. FRENETTE. (2016) ChemInform Abstract: SYNTHESIS OF β‐(TRIMETHYLSILYLOXY) THIO ETHERS AND β‐HYDROXY THIO ETHERS BY THE REACTION OF EPOXIDES WITH ARYL‐ AND ALKYLTHIOTRIMETHYLSILANES. Chemischer Informationsdienst 12:48.
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