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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 11
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Original Articles

The Oxidation of Secondary Alcohols to Ketones with Trichloroisocyanuric Acid

Gene A. Hiegel Department of Chemistry and Biochemistry, California State University, Fullerton, Fullerton, California, 92634
&
Malekashtar Nalbandy Department of Chemistry and Biochemistry, California State University, Fullerton, Fullerton, California, 92634
Pages 1589-1595 | Received 28 Jan 1992, Published online: 23 Sep 2006

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Mukka Satish Kumar, Kamatala Chinna Rajanna, Marri Venkateswarlu, Purugula Venkanna & Pondichery Kuppuswamy Saiprakash. (2015) Ultrasonically Assisted Rate Enhancements in Trichloroisocyanuric Acid/DMF/NaNO2 Triggered Nitration of Aromatic Compounds and Decarboxylative Nitration of α,β-Unsaturated Acids. Synthetic Communications 45:19, pages 2251-2258.
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Ping Zhong, Sheng-rong Guo & Cai-sheng Song. (2004) A Simple and Efficient Method for the Preparation of Heterocyclic N-Oxide. Synthetic Communications 34:2, pages 247-253.
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Ping Zhong, Meng-Ping Guo & Nan-Ping Huang. (2002) A SELECTIVE AND CONVENIENT OXIDATION OF ACETYLENIC SULFIDES TO ACETYLENIC SULFOXIDES USING TRICHLOROISOCYANURIC ACID. Synthetic Communications 32:2, pages 175-179.
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Ping Zhong & Meng-Ping Guo. (2001) PREPARATION OF DISULFIDES BY THE OXIDATION OF THIOLS USING TRICHLOROISOCYANURIC ACID. Synthetic Communications 31:12, pages 1825-1828.
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Ping Zhong & Meng-Ping Guo. (2001) PREPARATION OF DISELENIDES BY THE OXIDATION OF SELENOLS USING TRICHLOROISOCYANURIC ACID. Synthetic Communications 31:10, pages 1507-1510.
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Zi-Xing Xiong, Nan-Ping Huang & Ping Zhong. (2001) A SELECTIVE AND CONVENIENT OXIDATION OF SULFIDES TO SULFOXIDES WITH TRICHLOROISOCYANURIC ACID. Synthetic Communications 31:2, pages 245-248.
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GeneA. Hiegel, ChristopherD. Bayne, Yariv Donde, GeraldS. Tamashiro & LisaA. Hilberath. (1996) The Oxidation of Aldehydes to Methyl Esters using Trichloroisocyanuric Acid. Synthetic Communications 26:14, pages 2633-2639.
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Marta Benincasa, Romano Grandi, Franco Ghelfi & UgoM. Pagnoni. (1995) Oxidation of α-Acetoxy Acetals with Trichloroisocyanuric Acid. Synthetic Communications 25:21, pages 3463-3470.
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Shen Zhao, Shimin Yang, Guopeng Du, Daopeng Zhang, Hui Liu & Feng‐Gang Sun. (2022) ortho ‐Acylation of Aryl Iodides Enabled with Imides via Palladium/Norbornene/CuI Catalysis . Advanced Synthesis & Catalysis 364:20, pages 3506-3511.
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Kumar Dilip Ashtekar, Hadi Gholami, Mehdi Moemeni, Ankush Chakraborty, Lindsey Kiiskila, Xinliang Ding, Edmond Toma, Christopher Rahn & Babak Borhan. (2022) A Mechanistically Inspired Halenium Ion Initiated Spiroketalization: Entry to Mono‐ and Dibromospiroketals. Angewandte Chemie International Edition 61:8.
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Kumar Dilip Ashtekar, Hadi Gholami, Mehdi Moemeni, Ankush Chakraborty, Lindsey Kiiskila, Xinliang Ding, Edmond Toma, Christopher Rahn & Babak Borhan. (2022) A Mechanistically Inspired Halenium Ion Initiated Spiroketalization: Entry to Mono‐ and Dibromospiroketals. Angewandte Chemie 134:8.
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Sara Zahim, Kenny Delacroix, Agathe Carlier, Thierry Berranger, Julie Bergraser, Pierre-Georges Echeverria & Laurent Petit. (2021) Tetrahydro-4 H -pyran-4-one: From the Laboratory Scale to Pilot Plant Manufacture . Organic Process Research & Development 26:1, pages 199-206.
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Ashish Bhatt, Rajesh K. Singh, Bhupendra K. Sarma & Ravi Kant. (2019) Trichloroisocyanuric acid-mediated synthesis of 1,5-fused 1,2,4-triazoles from N-heteroaryl benzamidines via intramolecular oxidative N–N bond formation. Tetrahedron Letters 60:36, pages 151026.
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Irene Dip, Christina Gethers, Tonya Rice & Thomas S. Straub. (2018) Oxidation of 4- tert- Butylcyclohexanol with Swimming Pool Bleach . Journal of Chemical Education 96:1, pages 183-186.
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Bartosz Marciniak, Justyna Walkowiak-Kulikowska & Henryk Koroniak. (2017) On the halofluorination reactions of olefins as selective, and an efficient methodology for the introduction of fluorine into organic molecules. Journal of Fluorine Chemistry 203, pages 47-61.
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Irene Dip, Christina Gethers, Tonya Rice & Thomas S. Straub. (2017) A rapid and convenient oxidation of secondary alcohols. Tetrahedron Letters 58:28, pages 2720-2722.
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Kumar Dilip Ashtekar, Nastaran Salehi Marzijarani, Arvind Jaganathan, Daniel Holmes, James E. Jackson & Babak Borhan. (2014) A New Tool To Guide Halofunctionalization Reactions: The Halenium Affinity ( HalA ) Scale . Journal of the American Chemical Society 136:38, pages 13355-13362.
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Yuanyuan Jing, Constantin G. Daniliuc & Armido Studer. (2014) Direct Conversion of Alcohols to α-Chloro Aldehydes and α-Chloro Ketones. Organic Letters 16:18, pages 4932-4935.
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Claudio C. Silveira, Samuel R. Mendes, Guilherme M. Martins, Sheila C. Schlösser & Teodoro S. Kaufman. (2013) Modular CeCl3·7H2O-catalyzed multi-component synthesis of 1,2,3,4-tetrasubstituted pyrroles under microwave irradiation and their further trichloroisocyanuric acid-mediated conversion into 5-sulfenylpyrrole derivatives. Tetrahedron 69:43, pages 9076-9085.
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Gene A. Hiegel, Gianluca Pozzi & AnuMahadevan. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Claudio C. Silveira, Samuel R. Mendes, Lucas Wolf, Guilherme M. Martins & Lisandro von Mühlen. (2012) Efficient synthesis of 3-selanyl- and 3-sulfanylindoles employing trichloroisocyanuric acid and dichalcogenides. Tetrahedron 68:51, pages 10464-10469.
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Ruben P. van Summeren, Amy Romaniuk, Edwin G. IJpeij & Paul L. Alsters. (2012) The oxidation of alcohols with trichloroisocyanuric acid: pyridine from base to organocatalyst. Catalysis Science & Technology 2:10, pages 2052.
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Roya Azadi, Babak Mokhtari & Mohamad-Ali Makaremi. (2012) Phosphine-free conversion of alcohols into alkyl thiocyanates using trichloroisocyanuric acid/NH4SCN. Chinese Chemical Letters 23:1, pages 77-80.
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P. Mark L. Sandercock & Julie S. Barnett. (2009) Characterization of the Products Formed by the Reaction of Trichlorocyanuric Acid with 2-Propanol. Journal of Forensic Sciences 54:6, pages 1336-1340.
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Ahmad Khoramabadi‐Zad, Isaa Yavari, Azam Shiri & Azad Bani. (2009) Oxidation of bisnaphthols to spironaphthalenones, revisited. Journal of Heterocyclic Chemistry 45:5, pages 1351-1358.
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Gene A. Hiegel & Gianluca. Pozzi. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Aleksandra Siwicka, David Cuperly, Livio Tedeschi, Ronan Le Vézouët, Andrew J.P. White & Anthony G.M. Barrett. (2007) Total synthesis of the tricyclic skeleton of the natural Celastraceae sesquiterpenoids and related synthetic analogs. Tetrahedron 63:26, pages 5903-5917.
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Sudarsanan Varaprath & Debra H. Stutts. (2007) Utility of trichloroisocyanuric acid in the efficient chlorination of silicon hydrides. Journal of Organometallic Chemistry 692:10, pages 1892-1897.
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Jinxing Ye, Yongcan Wang, Jiping Chen & Xinmiao Liang. (2004) Trichloroisocyanuric Acid: A Convenient Oxidation Reagent for Phase‐Transfer Catalytic Epoxidation of Enones under Non‐Aqueous Conditions. Advanced Synthesis & Catalysis 346:6, pages 691-696.
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Afsaneh Safavi & Mohammad Ali Karimi. (2003) Flow-injection chemiluminescence determination of chlorinated isocyanuric acids. Analytical and Bioanalytical Chemistry 375:3, pages 424-427.
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Ulf Tilstam & Hilmar Weinmann. (2002) Trichloroisocyanuric Acid:  A Safe and Efficient Oxidant. Organic Process Research & Development 6:4, pages 384-393.
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Jeffrey B. Arterburn. (2001) Selective oxidation of secondary alcohols. Tetrahedron 57:49, pages 9765-9788.
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Amena Anjum & P. Srinivas. (2001) An Efficient and Mild Procedure for the Preparation of Benzoic Acids via Oxidation of Aromatic Carbonyl Compounds by Employing N -Bromoimides and Mercuric Acetate System . Chemistry Letters 30:9, pages 900-901.
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Lidia De Luca, Giampaolo Giacomelli & Andrea Porcheddu. (2001) A Very Mild and Chemoselective Oxidation of Alcohols to Carbonyl Compounds. Organic Letters 3:19, pages 3041-3043.
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Ulf Tilstam, Michael Harre, Thilo Heckrodt & Hilmar Weinmann. (2001) A mild and efficient dehydrogenation of indolines. Tetrahedron Letters 42:32, pages 5385-5387.
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Gene A. Hiegel. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Gerhard Knothe & Johannes DerksenPiet Bogaert, Theodoor Slaghek, Herman Feil & Patrick Tassignon. 1999. Recent Developments in the Synthesis of Fatty Acid Derivatives. Recent Developments in the Synthesis of Fatty Acid Derivatives 100 127 .
Patrick S.G. Tassignon, Dick de Wit, Theo C. de Rijk & Laurent F. De Buyck. (1995) Selective oxidation of primary-secondary diols with methyl hypochlorite in acid buffered medium. Tetrahedron 51:43, pages 11863-11872.
Crossref
. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 727 856 .
Kevin E.B. Parkes & Stewart K. Richardson. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 111 204 .
Kevin E.B. Parkes & Stewart K. Richardson. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 1 52 .
. 1995. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 220 241 .
G. A. HIEGEL & M. NALBANDY. (2010) ChemInform Abstract: The Oxidation of Secondary Alcohols to Ketones with Trichloroisocyanuric Acid.. ChemInform 24:1.
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