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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 32, 2002 - Issue 14
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Original Articles

OXIDATION OF BENZYL ALCOHOLS WITH OXONE® AND SODIUM BROMIDE

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Pages 2115-2123 | Received 18 Apr 2001, Published online: 18 Oct 2011

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Rathinavel Jagatheesan, Poovan Shanmugavelan, Subramaniyan Sambathkumar & Pugalenthi Ramesh. (2021) An expeditious and efficient method for the oxidation of benzyl alcohols by homogeneous electrolysis. Synthetic Communications 51:19, pages 3013-3022.
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Arash Ghorbani-Choghamarani, Mohammad Ali Zolfigol & Tahereh Azadbakht. (2010) 1,2-Dipyridiniumditribromide-ethane (DPTBE) as a New Oxidizing Agent for the Chemoselective Oxidation of Sulfides to the Sulfoxides. Phosphorus, Sulfur, and Silicon and the Related Elements 185:3, pages 573-577.
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Agnes Schulze, Georgia Pagona & Athanassios Giannis. (2006) Oxone/Sodium Chloride: A Simple and Efficient Catalytic System for the Oxidation of Alcohols to Symmetric Esters and Ketones. Synthetic Communications 36:9, pages 1147-1156.
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Rafael L. Oliveira, Krzysztof Nicinski, Marcin Pisarek, Agnieszka Kaminska, Arne Thomas, Grzegorz Pasternak & Juan C. Colmenares. (2022) Porous Heteroatom‐Doped Carbons: Efficient Catalysts for Selective Oxidation of Alcohols by Activated Persulfate. ChemCatChem 14:20.
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Ziman Cai, Xiangzhe Zeng, Yumeng Zhang, Yan Liu, Guo Tang & Yufen Zhao. (2022) Direct Synthesis of Dialkylphosphites from White Phosphorus. Advanced Synthesis & Catalysis 364:17, pages 2916-2921.
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Katelyn A. Leets, Angela Pacherille & John D. Chisholm. (2022) Tandem oxidation-bromination of allylic alcohols with a TEMPO-Oxone-Et4NBr reactant system. Tetrahedron Letters 103, pages 153994.
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Chenxi He, Foqing Ma, Wei Zhang & Rongbiao Tong. (2022) Reinvestigating FeBr 3 -Catalyzed Alcohol Oxidation with H 2 O 2 : Is a High-Valent Iron Species (HIS) or a Reactive Brominating Species (RBS) Responsible for Alcohol Oxidation? . Organic Letters 24:19, pages 3499-3503.
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Jiaquan Li, Fuping Li, Qi Yang, Shaobin Wang, Hongqi Sun, Qingning Yang, Junwang Tang & Shaomin Liu. (2021) Tailoring collaborative N–O functionalities of graphene oxide for enhanced selective oxidation of benzyl alcohol. Carbon 182, pages 715-724.
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Jiaquan Li, Shiyong Zhao, Lianji Zhang, San Ping Jiang, Shi‐Ze Yang, Shaobin Wang, Hongqi Sun, Bernt Johannessen & Shaomin Liu. (2021) Cobalt Single Atoms Embedded in Nitrogen‐Doped Graphene for Selective Oxidation of Benzyl Alcohol by Activated Peroxymonosulfate. Small 17:16.
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Derek Troiano, Valérie Orsat & Marie-Josée Dumont. (2020) Status of Biocatalysis in the Production of 2,5-Furandicarboxylic Acid. ACS Catalysis 10:16, pages 9145-9169.
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Jiaquan Li, Mengting Li, Hongqi Sun, Zhimin Ao, Shaobin Wang & Shaomin Liu. (2020) Understanding of the Oxidation Behavior of Benzyl Alcohol by Peroxymonosulfate via Carbon Nanotubes Activation. ACS Catalysis 10:6, pages 3516-3525.
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Guodong Zhao & Rongbiao Tong. (2019) A solvent-free catalytic protocol for the Achmatowicz rearrangement. Green Chemistry 21:1, pages 64-68.
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Sayan Sarkar, Piyali Sarkar & Pradyut Ghosh. (2018) Selective Single-Step Oxidation of Amine to Cross-Azo Compounds with an Unhampered Primary Benzyl Alcohol Functionality. Organic Letters 20:21, pages 6725-6729.
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Richard C. LarockRichard C. Larock, Anton V. Dubrovskiy & Nataliya A. Markina. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 137 .
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Chang-Qing Ruan, Maria Strømme, Albert Mihranyan & Jonas Lindh. (2017) Favored surface-limited oxidation of cellulose with Oxone® in water. RSC Advances 7:64, pages 40600-40607.
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Banothu Rammurthy, Peraka Swamy, Mameda Naresh, Kodumuri Srujana, Chevella Durgaiah, Gajula Krishna Sai & Nama Narender. (2017) A new and versatile one-pot strategy to synthesize alpha-bromoketones from secondary alcohols using ammonium bromide and oxone. New Journal of Chemistry 41:10, pages 3710-3714.
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Gennady I. Nikishin, Nadezhda I. Kapustina, Lyubov' L. Sokova, Oleg V. Bityukov & Alexander O. Terent'ev. (2017) One-pot oxidative bromination – Esterification of aldehydes to 2-bromoesters using cerium (IV) ammonium nitrate and lithium bromide. Tetrahedron Letters 58:4, pages 352-354.
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Zhilong Li & Rongbiao Tong. (2016) Catalytic Environmentally Friendly Protocol for Achmatowicz Rearrangement. The Journal of Organic Chemistry 81:11, pages 4847-4855.
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G. I. Nikishin, L. L. Sokova, A. O. Terent´ev & N. I. Kapustina. (2016) Primary alkanols: oxidative homocondensation in water and cross-condensation in methanol. Russian Chemical Bulletin 64:12, pages 2845-2850.
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A. John Bosco, S. Lawrence, C. Christopher, S. Radhakrishnan, A. Arul Joseph Rosario, S. Raja & D. Vasudevan. (2015) Redox-mediated oxidation of alcohols using Cl − /OCl − redox couple in biphasic media . Journal of Physical Organic Chemistry 28:9, pages 591-595.
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McKenzie L. Campbell, Samuel A. Rackley, Lauren N. Giambalvo & Daniel C. Whitehead. (2015) Vanadium (V) oxide mediated bromolactonization of alkenoic acids. Tetrahedron 71:23, pages 3895-3902.
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Mohammad Ali Nasseri, Arezou Mohammadinezhad & Mehri Salimi. (2014) A cellulose-supported Mn(salen)Cl complex as an efficient heterogeneous catalyst for the selective oxidation of benzylic alcohols. Journal of the Iranian Chemical Society 12:1, pages 81-86.
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McKenzie L. Campbell, Samuel A. Rackley, Lauren N. Giambalvo & Daniel C. Whitehead. (2014) Bromolactonization of alkenoic acids mediated by V2O5 via bromide to bromenium in situ oxidation. Tetrahedron Letters 55:41, pages 5680-5682.
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Katsuhiko Moriyama, Misato Takemura & Hideo Togo. (2014) Selective Oxidation of Alcohols with Alkali Metal Bromides as Bromide Catalysts: Experimental Study of the Reaction Mechanism. The Journal of Organic Chemistry 79:13, pages 6094-6104.
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Raju Thasan & Kulangiappar Kumarasamy. (2014) Electrochemical bromination and oxidation of alkyl aromatic compounds by two-phase electrolysis. Korean Journal of Chemical Engineering 31:3, pages 365-373.
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Maryam Mirza-Aghayan, Mahdieh Molaee Tavana & Rabah Boukherroub. (2014) Oxone/iron(II) sulfate/graphite oxide as a highly effective system for oxidation of alcohols under ultrasonic irradiation. Tetrahedron Letters 55:2, pages 342-345.
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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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Keshaba Nanda Parida, Samik Jhulki, Susovan Mandal & Jarugu Narasimha Moorthy. (2012) Oxidation of benzyl alcohols, benzyl halides, and alkylbenzenes with oxone. Tetrahedron 68:47, pages 9763-9768.
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Jack K. Crandall, Yian Shi, Christopher P. Burke & Benjamin R. Buckley. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Patrick T. Lang, Andrew M. Harned & Jane E. Wissinger. (2011) Oxidation of Borneol to Camphor Using Oxone and Catalytic Sodium Chloride: A Green Experiment for the Undergraduate Organic Chemistry Laboratory. Journal of Chemical Education 88:5, pages 652-656.
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Takayuki Yakura, Ayaka Ozono & Kohei Morimoto. (2011) An Efficient Catalytic Oxidation of p-Alkoxypenols to p-Quinones Using Tetrabutylammonium Bromide and Oxone. Chemical and Pharmaceutical Bulletin 59:1, pages 132-134.
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Li Zhang, Zhenggen Zha, Zhiyong Wang & Shengquan Fu. (2010) Aqueous electrosynthesis of carbonyl compounds and the corresponding homoallylic alcohols in a divided cell. Tetrahedron Letters 51:10, pages 1426-1429.
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Kamal Amani, Mohammad Ali Zolfigol, Arash Ghorbani-Choghamarani & Maryam Hajjami. (2008) Ferric nitrate in the presence of catalytic amounts of KBr or NaBr: an efficient and homoselective catalytic media for the selective oxidation of sulfides to sulfoxides. Monatshefte für Chemie - Chemical Monthly 140:1, pages 65-68.
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Mohammad Ali Zolfigol, Kamal Amani, Maryam Hajjami & Arash Ghorbani-Choghamarani. (2008) Selective and efficient oxidation of sulfides to sulfoxides using ammonium cerium (IV) nitrate in the presence of a catalytic amount of KBr or NaBr. Monatshefte für Chemie - Chemical Monthly 139:8, pages 895-899.
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Thasan Raju, Sankar Manivasagan, Balachandran Revathy, Kumarasamy Kulangiappar & Arunachalam Muthukumaran. (2007) A mild and efficient method for the oxidation of benzylic alcohols by two-phase electrolysis. Tetrahedron Letters 48:21, pages 3681-3684.
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Mohammad Ali Zolfigol, Farhad Shirini, Gholamabbas Chehardoli & Eskandar Kolvari. (2007) A catalytic and transition metal-free method for the chemoselective oxidation of alcohols to their corresponding carbonyl compounds using periodic acid or iodic acid in the presence of a catalytic amount of KBr. Journal of Molecular Catalysis A: Chemical 265:1-2, pages 272-275.
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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.
Alan Armstrong, Ian D. Edmonds, Martin E. Swarbrick & Nigel R. Treweeke. (2005) Electrophilic amination of enolates with oxaziridines: effects of oxaziridine structure and reaction conditions. Tetrahedron 61:35, pages 8423-8442.
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J.S Yadav, B.V.S Reddy, A.K Basak & A Venkat Narsaiah. (2004) Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents. Tetrahedron 60:9, pages 2131-2135.
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Mojtaba Bagherzadeh. (2003) A new and highly effective method for catalytic oxidation of alcohols to the corresponding carbonyl compounds using the tris[(2-oxazolinyl)phenolato]manganese(III)/Oxone®/n-Bu4NBr oxidation system. Tetrahedron Letters 44:50, pages 8943-8945.
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. (2002) Oxidation and Bromodehydroxymethylation of Benzylic Alcohols Using NaBrO 3 /NaHSO 3 Reagent . Bulletin of the Korean Chemical Society 23:11, pages 1667-1670.
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Bon‐Suk Koo, Chang Keun Lee & Kee‐Jung Lee. (2010) Oxidation of Benzyl Alcohols with Oxone® and Sodium Bromide.. ChemInform 33:45, pages 42-42.
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Rafael de Lima Oliveira, Krzysztof Nicinski, Marcin Pisarek, Agnieszka Kaminska, Arne Thomas, Grzegorz Pasternak & Juan C. Colmenares. (2022) Porous Heteroatom-Doped Carbons: Efficient Catalysts for Selective Oxidation of Alcohols by Activated Persulfate. SSRN Electronic Journal.
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