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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 21, 1991 - Issue 15-16
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Original Articles

Iodobenzene Dichloride - An Efficient Reagent for Preparation of Nitrile Oxides from Aldoximes

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Pages 1625-1629 | Received 23 Apr 1991, Published online: 23 Sep 2006

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Run-Kai Fang, Zheng-Chun Yin, Jun-Shen Chen & Guan-Wu Wang. (2022) [3 + 2] Cycloaddition reactions of nitrile oxides generated in situ from aldoximes with alkenes and alkynes under ball-milling conditions. Green Chemistry Letters and Reviews 15:3, pages 519-528.
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Anumula Raghupathi Reddy, Gilla Goverdhan, Aalla Sampath, Khagga Mukkanti, Padi Pratap Reddy & Rakeshwar Bandichhor. (2012) Application of [3 + 2]-Cycloaddition in the Synthesis of Valdecoxib. Synthetic Communications 42:5, pages 639-649.
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Articles from other publishers (41)

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Yasmin Saima & Saikat Khamarui. (2022) MnVI-NP–Catalyzed Generation of Nitrile Oxides: Easy Access to Isoxazolines and Isoxazoles via Stereoselective 1,3-Dipolar Cyclo­addition Reactions. SynOpen 06:03, pages 173-178.
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Md Imran Hossain, Md Imdadul H Khan, Seong Jong Kim & Hoang V Le. (2022) Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides. Beilstein Journal of Organic Chemistry 18, pages 446-458.
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Tania, Tiffany B. Poynder, Aishvaryadeep Kaur, Lachlan Barwise, Sevan D. Houston, Akshay J. Nair, Jack K. Clegg, David J. D. Wilson & Jason L. Dutton. (2021) PhICl 2 is activated by chloride ions . Dalton Transactions 50:34, pages 11986-11991.
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Tiffany B. Poynder, Analia I. Chamorro Orué, Tania, Lachlan Sharp-Bucknall, Matthew T. Flynn, David J. D. Wilson, Kasun S. Athukorala Arachchige, Jack K. Clegg & Jason L. Dutton. (2021) On the activation of PhICl 2 with pyridine . Chemical Communications 57:40, pages 4970-4973.
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Oksana B. Bondarenko & Nikolai V. Zyk. (2020) The main directions and recent trends in the synthesis and use of isoxazoles. Chemistry of Heterocyclic Compounds 56:6, pages 694-707.
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Akira Yoshimura, Melissa E. Jarvi, Michael T. Shea, Cody L. Makitalo, Gregory T. Rohde, Mekhman S. Yusubov, Akio Saito & Viktor V. Zhdankin. (2019) Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones. European Journal of Organic Chemistry 2019:39, pages 6682-6689.
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Xiaohua Zhen, Xintong Wan, Wei Zhang, Qiao Li, Daisy Zhang-Negrerie & Yunfei Du. (2019) Synthesis of Spirooxindoles from N -Arylamide Derivatives via Oxidative C(sp 2 )–C(sp 3 ) Bond Formation Mediated by PhI(OMe) 2 Generated in Situ . Organic Letters 21:4, pages 890-894.
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Mohd Waheed, Naseem Ahmed, Meshari A Alsharif, Mohammed Issa Alahmdi & Sayeed Mukhtar. (2019) PhI(OAc) 2 ‐Mediated One‐Pot Synthesis and their Antibacterial Activity of Flavone and Coumarin Based Isoxazoles Under Mild Reaction Conditions . ChemistrySelect 4:6, pages 1872-1878.
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Guodong Zhao, Lixin Liang, Chi Ho Ethan Wen & Rongbiao Tong. (2018) In Situ Generation of Nitrile Oxides from NaCl–Oxone Oxidation of Various Aldoximes and Their 1,3-Dipolar Cycloaddition. Organic Letters 21:1, pages 315-319.
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Akira Nakamura, Hodaka Kanou, Junki Tanaka, Akira Imamiya, Tomohiro Maegawa & Yasuyoshi Miki. (2018) A mild method for synthesizing carboxylic acids by oxidation of aldoximes using hypervalent iodine reagents. Organic & Biomolecular Chemistry 16:4, pages 541-544.
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Akira Yoshimura, Khiem C. Nguyen, Gregory T. Rohde, Pavel S. Postnikov, Mekhman S. Yusubov & Viktor V. Zhdankin. (2017) Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes. The Journal of Organic Chemistry 82:22, pages 11742-11751.
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Akira Yoshimura, Khiem C. Nguyen, Scott C. Klasen, Pavel S. Postnikov, Mekhman S. Yusubov, Akio Saito, Victor N. Nemykin & Viktor V. Zhdankin. (2016) Hypervalent Iodine‐Catalyzed Synthesis of 1,2,4‐Oxadiazoles from Aldoximes and Nitriles. Asian Journal of Organic Chemistry 5:9, pages 1128-1133.
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Rajesh Kumar, Manoj Kumar & Om Prakash. (2016) A Simple and Efficient Method for the Synthesis of Novel Pyrazolyl Isoxazoline Derivatives Using Hypervalent Iodine ( III ) Reagent . Heteroatom Chemistry 27:4, pages 228-234.
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Ankur Singhal, Santosh Kumar Reddy Parumala, Arun Sharma & Rama Krishna Peddinti. (2016) Hypervalent iodine mediated synthesis of di- and tri-substituted isoxazoles via [3+2] cycloaddition of nitrile oxides. Tetrahedron Letters 57:7, pages 719-722.
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Tabasum Ismail, Syed Shafi, Irfan Hyder, Tabasum Sidiq, Anamika Khajuria, Sarvar M. Alam & M. Sampath Kumar Halmuthur. (2015) Design and Synthesis of Novel 1,2,3‐Triazole‐ and 2‐Isoxazoline‐Based Bis ‐Heterocycles as Immune Potentiators . Archiv der Pharmazie 348:11, pages 796-807.
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Weidong Kong, Quanping Guo, Zhaoqing Xu, Guoqiang Wang, Xianxing Jiang & Rui Wang. (2015) Iodine(III)-Mediated Oxy-fluorination of Alkenyl Oximes: An Easy Path to Monofluoromethyl-Substituted Isoxazolines. Organic Letters 17:15, pages 3686-3689.
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Marco A. Ciufolini. (2014) Synthetic studies on heterocyclic natural products. Canadian Journal of Chemistry 92:3, pages 186-193.
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Akira Yoshimura, Kyle R. Middleton, Anthony D. Todora, Brent J. Kastern, Steven R. Koski, Andrey V. Maskaev & Viktor V. Zhdankin. (2013) Hypervalent Iodine Catalyzed Generation of Nitrile Oxides from Oximes and their Cycloaddition with Alkenes or Alkynes. Organic Letters 15:15, pages 4010-4013.
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Biswanath Das, Avula Satyakumar, Bommena Ravikanth, Bommena Vittal Rao, Tuniki Venugopal Raju, Busi Siddhardha & Upadyayula Suryanaryana Murty. (2013) Synthesis and Biological Activity of a Novel Pentacyclic Heterocycle. Journal of Heterocyclic Chemistry 50:2, pages 430-434.
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Sarah L Harding, Sebastian M Marcuccio & G Paul Savage. (2012) Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester. Beilstein Journal of Organic Chemistry 8, pages 606-612.
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Tim Jen, Brian A. Mendelsohn & Marco A. Ciufolini. (2010) Oxidation of α-Oxo-Oximes to Nitrile Oxides with Hypervalent Iodine Reagents. The Journal of Organic Chemistry 76:2, pages 728-731.
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Sandeep Bhosale, Santosh Kurhade, Samir Vyas, Venkata P. Palle & Debnath Bhuniya. (2010) Magtrieve™ (CrO2) and MnO2 mediated oxidation of aldoximes: studying the reaction course. Tetrahedron 66:50, pages 9582-9588.
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Huan Liang & Marco A. Ciufolini. (2010) Synthetic aspects of the oxidative amidation of phenols. Tetrahedron 66:31, pages 5884-5892.
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Zvi RappoportEdgars Abele & Edmunds Lukevics. 2010. Patai's Chemistry of Functional Groups. Patai's Chemistry of Functional Groups.
Mustafa J. Raihan, Veerababurao Kavala, Chun-Wei Kuo, B. Rama Raju & Ching-Fa Yao. (2010) ‘On-water’ synthesis of chromeno-isoxazoles mediated by [hydroxy(tosyloxy)iodo]benzene (HTIB). Green Chemistry 12:6, pages 1090.
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Harisadhan Ghosh & Bhisma K. Patel. (2010) Hypervalent iodine( iii )-mediated oxidation of aldoximes to N-acetoxy or N-hydroxy amides . Org. Biomol. Chem. 8:2, pages 384-390.
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Kuriya Madavu Lokanatha Rai. 2008. Synthesis of Heterocycles via Cycloadditions II. Synthesis of Heterocycles via Cycloadditions II 1 69 .
Mahmoud Mabrour, Khalid Bougrin, Rachid Benhida, André Loupy & Mohamed Soufiaoui. (2007) An efficient one-step regiospecific synthesis of novel isoxazolines and isoxazoles of N-substituted saccharin derivatives through solvent-free microwave-assisted [3+2] cycloaddition. Tetrahedron Letters 48:3, pages 443-447.
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Achim Hiller, Jörg T. Patt & Jörg Steinbach. (2006) NMR study on the structure and stability of 4‐substituted aromatic iodosyl compounds. Magnetic Resonance in Chemistry 44:10, pages 955-958.
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C. Escolano & S. Vázquez. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 685 704 .
David W. Knight & Glen A. Russell. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Julita Jóźwik, Malgorzata Kosior, Jaroslaw Kiegiel & Janusz Jurczak. (2001) Asymmetric induction in the 1,3‐dipolar cycloaddition of chiral nitrile oxide derived from (2 R )‐bornane‐10,2‐sultam . Chirality 13:10, pages 629-630.
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Jarosław Kiegiel, Magdalena Popławska, Julita Jóźwik, Małgorzata Kosior & Janusz Jurczak. (1999) New method of in situ generation of nitrile oxides by MnO2 oxidation of aldoximes. Tetrahedron Letters 40:30, pages 5605-5608.
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Anastasios Varvoglis. (1997) Chemical transformations induced by hypervalent iodine reagents. Tetrahedron 53:4, pages 1179-1255.
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Az-eddine Kella-Bennani, Mohamed Soufiaoui, Abdelali Kerbal, Souad Fkih-Tetouani & Najib Bitit. (1995) Synthesis of a novel tetracyclic heterocycle: 1-carboxy-13-oxo-[1,2,3]triazolo [1′,5′:4,3] [1,4]diazepino [6,7-c]chromane, using salicylaldehyde as a starting material. Tetrahedron 51:40, pages 10923-10928.
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