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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 13
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Original Articles

A SIMPLE AND PRACTICAL HALOGENATION OF ACTIVATED ARENES USING POTASSIUM HALIDE AND OXONE® IN WATER-ACETONITRILE MEDIUM

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Pages 2021-2027 | Received 13 Jun 2000, Published online: 09 Nov 2006

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James J. Palesch, Beau C. Gilles, Jared Chycota, Moriana K. Haj, Grant W. Fahnhorst & Jane E. Wissinger. (2019) Iodination of vanillin and subsequent Suzuki-Miyaura coupling: two-step synthetic sequence teaching green chemistry principles. Green Chemistry Letters and Reviews 12:2, pages 117-126.
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B. V. Tamhankar, Uday V. Desai, R. B. Mane, P. P. Kulkarni & P. P. Wadgaonkar. (2002) OXIDATION OF ALKYLCYANOHYDRAZINES TO AZO-BIS NITRILES USING OXONE®–POTASSIUM BROMIDE IN AQUEOUS MEDIUM. Synthetic Communications 32:23, pages 3643-3646.
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Hidayat Hussain, Ivan R. Green & Ishtiaq Ahmed. (2013) Journey Describing Applications of Oxone in Synthetic Chemistry. Chemical Reviews 113:5, pages 3329-3371.
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Yuuki Takada, Masayuki Hanyu, Kotaro Nagatsu & Toshimitsu Fukumura. (2012) Radiolabeling of aromatic compounds using K[ * Cl]Cl and OXONE ® . Journal of Labelled Compounds and Radiopharmaceuticals 55:10, pages 383-386.
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Zvi RappoportVidyadhar Jadhav, Min Young Park & Yong Hae Kim. 2010. Patai's Chemistry of Functional Groups. Patai's Chemistry of Functional Groups.
Anna Tsoukala, Lucia Liguori, Giovanni Occhipinti & Hans-René Bjørsvik. (2009) A novel simple and efficient bromination protocol for activated arenes. Tetrahedron Letters 50:7, pages 831-833.
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U.V. Desai, D.M. Pore, B.V. Tamhankar, S.A. Jadhav & P.P. Wadgaonkar. (2006) An efficient deprotection of dithioacetals to carbonyls using Oxone–KBr in aqueous acetonitrile. Tetrahedron Letters 47:48, pages 8559-8561.
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Jack K. Crandall, Yian Shi & Christopher P. Burke. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Dipannita Kalyani, Allison R. Dick, Waseem Q. Anani & Melanie S. Sanford. (2006) A Simple Catalytic Method for the Regioselective Halogenation of Arenes. Organic Letters 8:12, pages 2523-2526.
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Michael B. Smith. 2003. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 367 376 .
. (2002) Bromination of Activated Arenes by Oxone? and Sodium Bromide. Bulletin of the Korean Chemical Society 23:5, pages 773-775.
Crossref
B. V. Tamhankar, Uday V. Desai, R. B. Mane, P. P. Wadgaonkar & Ashutosh V. Bedekar. (2010) ChemInform Abstract: A Simple and Practical Halogenation of Activated Arenes Using Potassium Halide and Oxone ® in Water—Acetonitrile Medium. . ChemInform 32:47.
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