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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 3
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Original Articles

Ruthenium Tetroxide Oxidation of Simple Ethers: A Systematic Study

Amos B. Smith III The Department of Chemistry, The Monell Chemical Senses Center and The Laboratory for Research on the Structure of Matter
&
Robert M. Scarborough Jr. The University of Pennsylvania Philadelphia, Pennsylvania, 19104
Pages 205-211 | Published online: 05 Dec 2006

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Zdzislaw Paryzek & Iwona Skiera. (2007) SYNTHESIS AND CLEAVAGE OF LACTONES AND THIOLACTONES. APPLICATIONS IN ORGANIC SYNTHESIS. A REVIEW. Organic Preparations and Procedures International 39:3, pages 203-296.
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Fu-Chu Liu, Zhen-Qi Mei, You-Chu Wang & Jun Lin. (1997) SYNTHESES AND STEREOCHEMISTRY OF TETRAHYDROFURAN DERIVATIVES FROM α-PINENE. Organic Preparations and Procedures International 29:4, pages 473-476.
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Articles from other publishers (64)

Iunia Podolean, Simona M. Coman, Cristina Bucur, Cristian Teodorescu, Stefanos Kikionis, Efstathia Ioannou, Vassilios Roussis, Ana Primo, Hermenegildo Garcia & Vasile I. Parvulescu. (2022) Catalytic transformation of the marine polysaccharide ulvan into rare sugars, tartaric and succinic acids. Catalysis Today 383, pages 345-357.
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Yuichiro Kawamoto, Hideki Kitsukawa, Toyoharu Kobayashi & Hisanaka Ito. (2021) Total Synthesis of Nesteretal A. Organic Letters 23:18, pages 7074-7078.
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Xin Xiong, Yikang Wu & Bo Liu. (2020) Synthesis and Configuration of a p ‐Aminoacetophenonic Acid Isolated from Endophyte of the Mangrove Plant Kandel candel . European Journal of Organic Chemistry 2020:31, pages 5009-5018.
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Ashish Kumar Verma, Ande Chennaiah, Sateesh Dubbu & Yashwant D. Vankar. (2018) Stereoselective synthesis of sugar-fused (or 1,2-annulated) isochromans and isochromanones by using oxa-Pictet–Spengler reaction. Organic & Biomolecular Chemistry 16:37, pages 8258-8262.
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Richard C. LarockRichard C. Larock & Tuanli Yao. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 85 .
Iunia Podolean, Cristina Rizescu, Camelia Bala, Lucian Rotariu, Vasile I. Parvulescu, Simona M. Coman & Hermenegildo Garcia. (2016) Unprecedented Catalytic Wet Oxidation of Glucose to Succinic Acid Induced by the Addition of n ‐Butylamine to a Ru III Catalyst . ChemSusChem 9:17, pages 2307-2311.
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Rajendra D. Patil & Yoel Sasson. (2016) Naphthalenes Oxidation by Aqueous Sodium Hypochlorite Catalyzed by Ruthenium Salts Under Phase-Transfer Catalytic Conditions. Catalysis Letters 146:5, pages 991-997.
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Di Liu & Christopher W. Bielawski. (2016) Post-polymerization modification of poly(vinyl ether)s: a Ru-catalyzed oxidative synthesis of poly(vinyl ester)s and poly(propenyl ester)s. Polymer Chemistry 7:1, pages 63-68.
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Jian‐Bo Feng & Xiao‐Feng Wu. (2014) Transition metal‐catalyzed oxidative transformations of methylarenes. Applied Organometallic Chemistry 29:2, pages 63-86.
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Nobuki Kato, Yu Hamaguchi, Naoki Umezawa & Tsunehiko Higuchi. (2015) Efficient oxidation of ethers with pyridine N-oxide catalyzed by ruthenium porphyrins. Journal of Porphyrins and Phthalocyanines 19:01-03, pages 411-416.
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Yi Zhao, Angela Wan Ting Ng & Ying-Yeung Yeung. (2014) Mild propargylic oxidation using a diacetoxyiodobenzene/tert-butyl hydroperoxide protocol. Tetrahedron Letters 55:31, pages 4370-4372.
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Angela Gonzalez-de-Castro, Craig M. Robertson & Jianliang Xiao. (2014) Dehydrogenative α-Oxygenation of Ethers with an Iron Catalyst. Journal of the American Chemical Society 136:23, pages 8350-8360.
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Vincenzo Piccialli. (2014) Ruthenium Tetroxide and Perruthenate Chemistry. Recent Advances and Related Transformations Mediated by Other Transition Metal Oxo-species. Molecules 19:5, pages 6534-6582.
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Y. Obora & Y. Ishii. 2014. Comprehensive Organic Synthesis II. Comprehensive Organic Synthesis II 262 276 .
Victor S. Martín, José M. Palazón, Carmen M. Rodríguez, C. Richard NevillJrJr & Douglas K. Hutchinson. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Vincenzo Piccialli, Stefano D'Errico, Nicola Borbone, Giorgia Oliviero, Roberto Centore & Sabrina Zaccaria. (2013) A General Synthesis of Bis‐α‐acyloxy‐1,4‐ and ‐1,5‐diketones Through Catalytic Oxidative Opening of Acylated THF and THP Diols. European Journal of Organic Chemistry 2013:9, pages 1781-1789.
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Yi Zhao, Jascelyn Qian Lin Ang, Angela Wan Ting Ng & Ying-Yeung Yeung. (2013) Oxidative transformation of cyclic ethers/amines to lactones/lactams using a DIB/TBHP protocol. RSC Advances 3:43, pages 19765.
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Vincenzo Piccialli, Sabrina Zaccaria, Giorgia Oliviero, Stefano D'Errico, Valentina D'Atri & Nicola Borbone. (2012) Insight into Pyridinium Chlorochromate Chemistry: Catalytic Oxidation of Tetrahydrofuran Compounds and Synthesis of Umbelactone. European Journal of Organic Chemistry 2012:23, pages 4293-4305.
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Dana V?lkov?Laurent Grasset & Andr? Ambl?s. (2009) Molecular compounds generated by ruthenium tetroxide oxidation and preparative off line thermochemolysis of lignite humic acids from South Moravia: Implications for molecular structure. Fuel 88:11, pages 2113-2121.
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Amos B. Smith, III, III, Todd Bosanac & Kallol Basu. (2009) Evolution of the Total Synthesis of (−)-Okilactomycin Exploiting a Tandem Oxy-Cope Rearrangement/Oxidation, a Petasis−Ferrier Union/Rearrangement, and Ring-Closing Metathesis. Journal of the American Chemical Society 131:6, pages 2348-2358.
Crossref
William P. GriffithWilliam P. Griffith. 2011. Ruthenium Oxidation Complexes. Ruthenium Oxidation Complexes 227 252 .
William P. GriffithWilliam P. Griffith. 2011. Ruthenium Oxidation Complexes. Ruthenium Oxidation Complexes 1 134 .
Ganesh Pandey, Madhesan Balakrishnan & Pandrangi Siva Swaroop. (2008) A Suzuki Cross‐Coupling and Intramolecular Aza‐Michael Addition Reaction Sequence Towards the Synthesis of 1,10b‐ epi ‐7‐Deoxypancratistatins and Their Cytotoxicity Studies . European Journal of Organic Chemistry 2008:34, pages 5839-5847.
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J. Stephen Clark, Carl A. Baxter, Alexander G. Dossetter, Stéphane Poigny, José L. Castro & William G. Whittingham. (2008) Stereoselective Construction of the Tricyclic Core of Neoliacinic Acid. The Journal of Organic Chemistry 73:3, pages 1040-1055.
Crossref
Helena M. C. Ferraz & Luiz S. Longo. (2007) Bicyclic β-Hydroxytetrahydrofurans as Precursors of Medium Ring Keto-Lactones. The Journal of Organic Chemistry 72:8, pages 2945-2950.
Crossref
Faiz Ahmed Khan, Vineet Dwivedi & Bhimsen Rout. (2007) Synthesis of a novel, bowl-like bis γ-lactone. Tetrahedron Letters 48:2, pages 207-209.
Crossref
Louis F. Fieser, Mary Fieser & Tse‐Lok HoTse‐Lok Ho, Mary Fieser, Louis Fieser & Janice Smith. 2006. Fieser and Fieser's Reagents for Organic Synthesis. Fieser and Fieser's Reagents for Organic Synthesis.
Victor S. Martín, José M. Palazón, Carmen M. Rodríguez & C. Richard NevillJr.Jr.. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Veljko Dragojlovi?Sne?ana Bajc, Andr? Ambl?s & Dragomir Vitorovi?. (2005) Ether and ester moieties in Messel shale kerogen examined by hydrolysis/ruthenium tetroxide oxidation/hydrolysis. Organic Geochemistry 36:1, pages 1-12.
Crossref
Luca Gonsalvi, Isabel W. C. E. Arends, Pasi Moilanen & Roger A. Sheldon. (2003) The Effect of pH Control on the Selective Ruthenium‐Catalyzed Oxidation of Ethers and Alcohols with Sodium Hypochlorite. Advanced Synthesis & Catalysis 345:12, pages 1321-1328.
Crossref
Helena M. C. Ferraz & Luiz S. Longo. (2003) Efficient Entry into Medium-Ring Keto-Lactones. The Ruthenium Tetraoxide-Promoted Oxidative Cleavage of β-Hydroxyethers. Organic Letters 5:8, pages 1337-1339.
Crossref
Thomas Straub & Ari M.P Koskinen. (2002) Catalytic oxidation of THF with homo and hetero metallic Mo/Ru complexes and molecular oxygen. Inorganic Chemistry Communications 5:12, pages 1052-1055.
Crossref
Chisato Mukai, Haruhisa Yamashita, Misato Sassa & Miyoji Hanaoka. (2002) Synthesis of oxaspiro[m.n] skeletons based on the Nicholas reaction. Tetrahedron 58:14, pages 2755-2762.
Crossref
Goverdhan Mehta & Ramdas Vidya. (2001) Oxa Bowls:  Studies Toward Hexaoxa-[6]-peristylane. Synthesis of a Seco -Derivative of Hexaoxa-[6]-peristylane . The Journal of Organic Chemistry 66:21, pages 6913-6918.
Crossref
Victor S. Martín, José M. Palazón & Carmen M. Rodríguez. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Leo A. Paquette, Dafydd R. Owen, Richard Todd Bibart, Christopher K. Seekamp, Alexandra L. Kahane, James C. Lanter & Miriam Alvarez Corral. (2001) 1-Oxaspiro[4.4]nonan-6-ones. Synthetic Access via Oxonium Ion Technology, Optical Resolution, and Conversion into Enantiopure Spirocyclic α,β-Butenolides. The Journal of Organic Chemistry 66:8, pages 2828-2834.
Crossref
Michael E Jung & Christopher P Lee. (2000) Use of the non-aldol aldol process in the synthesis of the C1–C11 fragment of the tedanolides: use of lactol ethers in place of tetrahydrofurans. Tetrahedron Letters 41:50, pages 9719-9723.
Crossref
Shatrughan P. Shahi, Anuradha Gupta, Sangeeta V. Pitre, M. Venkat Ram Reddy, R. Kumareswaran & Yashwant D. Vankar. (1999) Trimethylsilylnitrate−Chromium Trioxide and Trimethylsilylnitrate−DMSO:  Novel Reagent Systems for One Step Conversion of Olefins into α-Nitro Ketones and Cyclic Ethers into Lactones 1 . The Journal of Organic Chemistry 64:12, pages 4509-4511.
Crossref
Michael E. Jung, Usama Karama & Rodolfo Marquez. (1999) Conversion of Homoallylic Alcohols with Alkene Protection to the Corresponding Methyl Ketones. The Journal of Organic Chemistry 64:2, pages 663-665.
Crossref
Anna Maria Romano & Marco Ricci. (1997) New efficient catalysts for the aerobic oxidation of ethers. Journal of Molecular Catalysis A: Chemical 120:1-3, pages 71-74.
Crossref
Goverdhan Mehta, Faiz Ahmed Khan, Biswajit Ganguly & Jayaraman Chandrasekhar. (1994) π-Facial diastereoselection in reductions of sterically unbiased ketones containing the norbornyl framework: further tests for theoretical models. J. Chem. Soc., Perkin Trans. 2:11, pages 2275-2277.
Crossref
Pei Li & Howard Alper. (1992) Cobalt-catalyzed oxidation of ethers using oxygen. Journal of Molecular Catalysis 72:2, pages 143-152.
Crossref
E.S. Gore. 1991. Chemistry of the Platinum Group Metals - Recent Developments. Chemistry of the Platinum Group Metals - Recent Developments 180 235 .
Christopher R.A. Godfrey. 1991. Comprehensive Organic Synthesis. Comprehensive Organic Synthesis 235 250 .
A. Tenaglia, E. Terranova & B. Waegell. (1990) Ruthenium-catalysed C–H bond activation. Evidence for a concerted mechanism in oxyfunctionalization of cyclic saturated hydrocarbons. J. Chem. Soc., Chem. Commun.:19, pages 1344-1345.
Crossref
M. Bressan & A. Morvillo. 1990. New Developments in Selective Oxidation. New Developments in Selective Oxidation 119 124 .
Zafeer Ahmad, Uttam Kumar Ray & R.V. Venkateswaran. (1990) Synthesis of hexahydrobenzopyranones : bicyclic precursor lactones to the trichothecenes. Tetrahedron 46:3, pages 957-966.
Crossref
Hiroshi Suginome & Shinji Yamada. (1987) Synthesis of Some Five- and Six-Membered Oxasteroids of Cholestane Series by Ring Contraction and the Mass Spectrometric Fragmentations of Oxasteroids. Bulletin of the Chemical Society of Japan 60:7, pages 2453-2461.
Crossref
Hiroshi Hirota, Akihisa Yokoyama, Katsuaki Miyaji, Toshio Nakamura & Takeyoshi Takahashi. (1987) Synthetic studies on quassinoids: Total synthesis of (?)-amarolide. Tetrahedron Letters 28:4, pages 435-438.
Crossref
Penny A Chaloner. 1986. Handbook of Coordination Catalysis in Organic Chemistry. Handbook of Coordination Catalysis in Organic Chemistry 451 679 .
John L. Courtney. 1986. Organic Syntheses by Oxidation with Metal Compounds. Organic Syntheses by Oxidation with Metal Compounds 445 467 .
Herbert Frauenrath & Thomas Philipps. (2006) Diastereoselektive Synthese von cis ‐ oder trans ‐2,3‐substituierten Tetrahydrofuranen und 3,4‐substituierten 4‐Butanoliden . Liebigs Annalen der Chemie 1985:10, pages 1951-1961.
Crossref
Tsutomu Kojima, Yoshinobu Inouye & Hiroshi Kakisawa. (1985) Effective Cleavage of 7-Alkoxytricyclo[6.4.0.02,7]dodecan-3-one System. Bulletin of the Chemical Society of Japan 58:6, pages 1738-1740.
Crossref
G Balavoine, C Eskenazi & F Meunier. (1985) Oxydation catalytique d'éthers par le systéme RuCl3/NaOCl. Journal of Molecular Catalysis 30:1-2, pages 125-133.
Crossref
Tetsuji Kametani, Tadashi Katoh, Masayoshi Tsubuki & Toshio Honda. (1985) A FACILE PREPARATION OF ECDYSONE SIDE CHAIN BY UTILIZING FURAN DERIVATIVE. Chemistry Letters 14:4, pages 485-488.
Crossref
Roger Sheldon. (2010) Catalytic Oxidations in Organic Synthesis. Bulletin des Sociétés Chimiques Belges 94:9, pages 651-670.
Crossref
Sigeru Torii, Tsutomu Inokuchi & Takao Yukawa. (1984) INDIRECT ELECTROOXIDATION OF N -PROTECTED AMINES TO AMIDES WITH A DOUBLE MEDIATORY SYSTEM CONSISTING OF RuO4, AND Cl+ . Chemistry Letters 13:7, pages 1063-1066.
Crossref
Narayani Mallya & Ralph A. Zingaro. (1984) Ruthenium tetroxide — a reagent with the potential for the study of oxygen functionalities in coal. Fuel 63:3, pages 423-425.
Crossref
. 1984. Comprehensive Heterocyclic Chemistry. Comprehensive Heterocyclic Chemistry 781 867 .
D.R. Boyd. 1984. Comprehensive Heterocyclic Chemistry. Comprehensive Heterocyclic Chemistry 547 592 .
Louis S. Hegedus. (1982) Transition metals in organic synthesis annual survey covering the year 1980. Journal of Organometallic Chemistry 237, pages 231-450.
Crossref
K.R. Seddon. (1982) Ruthenium. Coordination Chemistry Reviews 41, pages 79-157.
Crossref
ROGER A. SHELDON & JAY K. KOCHI. 1981. Metal-catalyzed Oxidations of Organic Compounds. Metal-catalyzed Oxidations of Organic Compounds 350 386 .
A. B. III SMITH & R. M. JUN. SCARBOROUGH. (2016) ChemInform Abstract: RUTHENIUM TETROXIDE OXIDATION OF SIMPLE ETHERS: A SYSTEMATIC STUDY. Chemischer Informationsdienst 11:36.
Crossref

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