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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 15
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Original Articles

Efficient and Selective Mono and Dinitration of Phenols With Cr(NO3)3·2N2O4 as a New Nitrating Agent

Nasser Iranpoor Department of Chemistry, College of Science, Shiraz University, Shiraz, 71454, Iran
,
Habib Firouzabadi Department of Chemistry, College of Science, Shiraz University, Shiraz, 71454, Iran
&
Mohammad AliZolfigol Department of Chemistry, College of Science, University of Bu-Ali Sina, Hamadan, 65174, Iran
Pages 2773-2781 | Received 27 Jan 1998, Published online: 20 Aug 2006

Citations (36)

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Nasser Iranpoor, Habib Firouzabadi, Reza Heydari & Morteza Shiri. (2005) Nitration of Aromatic Compounds by Zn(NO3)2 · 2N2O4 and Its Charcoal‐Supported System. Synthetic Communications 35:2, pages 263-270.
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Mohammad Ali Zolfigol, Farhad Shirini & Arash Ghorbani Chogamarani. (2003) Silica Chloride/NaNO2 as a Novel Heterogeneous System for the Nitration of Phenols Under Mild Conditions. Phosphorus, Sulfur, and Silicon and the Related Elements 178:9, pages 2019-2025.
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R. Rajagopal & K. V. Srinivasan. (2003) Regio-selective Mono Nitration of Phenols with Ferric Nitrate in Room Temperature Ionic Liquid. Synthetic Communications 33:6, pages 961-966.
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Mohammad Ali Zolfigol, Mohammad Hassan Zebarjadian, Iraj Mohammadpoor-Baltork & Mojtaba Shamsipur. (2002) DEPROTECTION OF 1,1-DIACETATES WITH [NO+ ⋅ CROWN ⋅ H(NO3)2 −]. Synthetic Communications 32:18, pages 2803-2808.
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Vandana Bansal & R. N. Khanna. (2002) REGIOSELECTIVE MONONITRATION OF COUMARINS USING CHROMIUM NITRATE AS NITRATING AGENT. Synthetic Communications 32:9, pages 1345-1350.
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Mohammad Ali Zolfigol, Mohammad Hassan Zebarjadian, Majid M. Sadegh, Iraj Mohammadpoor-Baltork, Hamid Reza Memarian & Mojtaba Shamsipur. (2001) CHEMOSELECTIVE OXIDATION OF 1,4-DIHYDROPYRIDINES WITH [NO+.CROWN.H(NO3)2 −]. Synthetic Communications 31:6, pages 929-934.
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Mohammad Ali Zolfigol, Maryam Kiany Borazjani, ShadpourE Mallakpour & Hossein Nasr-isfahani. (2000) An Efficient Method for the Oxidation of Urazoles Under Mild and Heterogeneous Conditions. Synthetic Communications 30:14, pages 2573-2585.
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Mohammad Ali Zolfigol, Ezat Ghaemi & Elahe Madrakian. (2000) A Convenient Method for Selective Mono or Dinitration of Phenol under Mild Conditions. Synthetic Communications 30:10, pages 1689-1694.
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N. Iranpoor, H. Firouzabadi & R. Heydari. (1999) Ionic Complex of N2 O4 with 18-Crown-6: A Highly Efficient and Selective Reagent for Nitration of Phenols. Synthetic Communications 29:19, pages 3295-3302.
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Articles from other publishers (27)

A. Makhloufi, O. Belhadad, R. Ghemit, M. Baitiche, M. Merbah & DJ. Benachour. (2018) Theoretical and conceptual density functional theory (DFT) study on selectivity of 4-hydroxyquinazoline electrophilic aromatic nitration. Journal of Molecular Structure 1152, pages 248-256.
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Hemchandra K. Chaudhari, Akshata Pahelkar & Balaram S. Takale. (2017) Preparative-scale synthesis of amino coumarins through new sequential nitration and reduction protocol. Tetrahedron Letters 58:43, pages 4107-4110.
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Yinchun Jiao, Man Zhu, Renjie Deng, Jian Jian, Yi Yin & Kuiyi You. (2017) Sulfated SO4 2−/WO3 as an efficient and eco-friendly catalyst for solvent-free liquid phase nitration of toluene with NO2. Research on Chemical Intermediates 43:7, pages 3961-3974.
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Ardeshir Khazaei, Mohammad Ali Zolfigol, Saied Alaie, Saeed Baghery, Babak Kaboudin, Yadollah Bayat & Asiye Asgari. (2016) {[MIM-NO 2 ]C(NO 2 ) 3 } a unique nano ionic liquid: application to the synthesis of novel Biginelli-type compounds . RSC Advances 6:12, pages 10114-10125.
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Saad S. Elmorsy, Saad Shaaban, Fathy Eldesoky & Ezzat Kandeel. (2015) Zinc Chloride Catalyzed Regioselective Nitration of Aromatic Hydrocarbons Using Tetrachlorosilane-Sodium Nitrate Homogeneous System. International Journal of Organic Chemistry 05:02, pages 49-56.
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Eslam Salahifar, Davood Nematollahi, Amir Mahyari & Keyvan Nosratzadegan. (2015) A Green and Safe Galvanostatic Method for the Synthesis of 4-Nitrocatechol in Aqueous Solution. Journal of The Electrochemical Society 162:6, pages G19-G24.
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Shuwen Gong, Lijun Liu, Junling Zhang & Qingxin Cui. (2014) Stable and eco-friendly solid acids as alternative to sulfuric acid in the liquid phase nitration of toluene. Process Safety and Environmental Protection 92:6, pages 577-582.
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Hassan Hosseini-Monfared, Hannaneh Falakian, Rahman Bikas & Peter Mayer. (2013) Intramolecular hydrogen bond effect on keto-enolization of aroylhydrazone in copper(II) complexes. Inorganica Chimica Acta 394, pages 526-534.
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Najmeh Nowrouzi, Abdol Mohammad Mehranpour, Elham Bashiri & Zohre Shayan. (2012) Aromatic nitration under neutral conditions using N-bromosuccinimide/silver(I) nitrate. Tetrahedron Letters 53:36, pages 4841-4842.
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Xiaoming Ma, Bindong Li, Chunxu Lv, Ming Lu, Jian Wu & Linjie Liang. (2011) An Efficient and Eco-friendly MoO3–SiO2 Solid Acid Catalyst for Electrophilic Aromatic Nitration with N2O5. Catalysis Letters 141:12, pages 1814-1820.
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Morteza Shiri, Mohammad Ali Zolfigol, Hendrik Gerhardus Kruger & Zahra Tanbakouchian. (2010) Advances in the application of N2O4/NO2 in organic reactions. Tetrahedron 66:47, pages 9077-9106.
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Guangbin Cheng, Xuelei Duan, Xiufang Qi & Chunxu Lu. (2008) Nitration of aromatic compounds with NO2/air catalyzed by sulfonic acid-functionalized ionic liquids. Catalysis Communications 10:2, pages 201-204.
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R Sabnis. 2007. Handbook of Acid-Base Indicators. Handbook of Acid-Base Indicators 115 138 .
Nitin S. Nandurkar, Mayur J. Bhanushali, Sachin R. Jagtap & Bhalchandra M. Bhanage. (2007) Ultrasound promoted regioselective nitration of phenols using dilute nitric acid in the presence of phase transfer catalyst. Ultrasonics Sonochemistry 14:1, pages 41-45.
Crossref
Nasser Iranpoor, Habib Firouzabadi, Najmeh Nowrouzi & Dena Firouzabadi. (2006) Highly chemoselective nitration of aromatic amines using the Ph3P/Br2/AgNO3 system. Tetrahedron Letters 47:38, pages 6879-6881.
Crossref
V. Anuradha, P.V. Srinivas, P. Aparna & J. Madhusudana Rao. (2006) p-Toluenesulfonic acid catalyzed regiospecific nitration of phenols with metal nitrates. Tetrahedron Letters 47:28, pages 4933-4935.
Crossref
Mohammad A. Zolfigol, Ezat Ghaemi, Elaheh Madrakian & Arash G. Choghamarani. (2006) 1,3-Dihalo-5,5-dimethylhydantoin or citric acid/NaNO2 as a heterogeneous system for the selective mononitration of phenols under mild conditions. Mendeleev Communications 16:1, pages 41-42.
Crossref
Xianghua Yang, Chanjuan Xi & Yanfeng Jiang. (2005) Regioselective nitration of N,N-dialkylanilines using cerium(IV) ammonium nitrate in acetonitrile. Tetrahedron Letters 46:50, pages 8781-8783.
Crossref
. (2004) Nitration of Aromatic Compounds on Silica Sulfuric Acid. Bulletin of the Korean Chemical Society 25:9, pages 1414-1416.
Crossref
H Firouzabadi, N Iranpoor & M Shiri. (2003) Direct and regioselective iodination and bromination of benzene, naphthalene and other activated aromatic compounds using iodine and bromine or their sodium salts in the presence of the Fe(NO3)3·1.5N2O4/charcoal system. Tetrahedron Letters 44:49, pages 8781-8785.
Crossref
Min Shi & Shi‐Cong Cui. (2003) A New Method for Nitration of Phenolic Compounds. Advanced Synthesis & Catalysis 345:11, pages 1197-1202.
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Ashutosh V. Joshi, Mubeen Baidoosi, Sudip Mukhopadhyay & Yoel Sasson. (2002) Nitration of Phenol and Substituted Phenols with Dilute Nitric Acid Using Phase-Transfer Catalysts. Organic Process Research & Development 7:1, pages 95-97.
Crossref
Mohammad Ali ZolfigolMohammad Hassan ZebarjadianGholamabbas ChehardoliHassan KeypourSadegh SalehzadehMojtaba Shamsipur. (2001) N-Nitrosation of Secondary Amines with [NO + ·Crown·H(NO 3 ) 2 - ] . The Journal of Organic Chemistry 66:10, pages 3619-3620.
Crossref
Mohammad Ali Zolfigol, Mohammad Hassan Zebarjadian, Gholamabbas Chehardoli, Shadpour E Mallakpour & Mojtaba Shamsipur. (2001) An efficient method for the oxidation of urazoles with [NO+·crown·H(NO3)2−]. Tetrahedron 57:8, pages 1627-1629.
Crossref
John M. Mellor, Stifun Mittoo, Rachel Parkes & Ross W. Millar. (2000) Improved Nitrations Using Metal Nitrate–Sulfuric Acid Systems. Tetrahedron 56:40, pages 8019-8024.
Crossref
Sariah Sana, K C Rajanna, Mir Moazzam Ali & P K Saiprakash. (2000) Mild, Efficient and Selective Nitration of Anilides, Non-Activated and Moderately Activated Aromatic Compounds with Ammonium Molybdate and Nitric Acid as a New Nitrating Agent. Chemistry Letters 29:1, pages 48-49.
Crossref
N. IRANPOOR, H. FIROUZABADI & M. A. ZOLFIGOL. (2010) ChemInform Abstract: Efficient and Selective Mono‐ and Dinitration of Phenols with Cr(NO 3 ) 3 ×2N 2 O 4 as a New Nitrating Agent. . ChemInform 29:43.
Crossref

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