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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 2
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Original Articles

α‐Chlorination of Acetophenones Using 1,3‐Dichloro‐5,5‐Dimethylhydantoin

Zijin Xu Department of Chemistry, East China Normal University, Shanghai, China
,
Deyan Zhang, Department of Chemistry, East China Normal University, Shanghai, China
&
Xinzhuo Zou Department of Chemistry, East China Normal University, Shanghai, ChinaCorrespondence[email protected]
Pages 255-258 | Received 30 May 2005, Published online: 15 Aug 2006

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Bin Zhou, Zizhan Chen, Zubiao Zheng, Bingbing Han & Xinzhuo Zou. (2012) One-Step Conversion of Acetophenones to α-Haloacetophenone Dimethyl Acetals Using DCDMH/DBDMH and Molecular Sieve in Methanol. Synthetic Communications 42:10, pages 1445-1453.
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Hojat Veisi, Ramin Ghorbani-Vaghei & Mohamad Ali Zolfigol. (2011) Recent Progress in the Use of N-Halo Compounds in Organic Synthesis. Organic Preparations and Procedures International 43:6, pages 489-540.
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Articles from other publishers (25)

James S. Sharley, Guido Gambacorta, Ana María Collado Pérez, Estela Espinos Ferri, Amadeo Fernandez Miranda, Isabelle Fernández Fernández, Jorge Sanchez Quesada & Ian R. Baxendale. (2022) A simple one-pot oxidation protocol for the synthesis of dehydrohedione from Hedione. Tetrahedron 126, pages 133068.
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Vaibhav Pramod CharpeMahima GuptaKuo Chu Hwang. (2022) Visible‐Light‐Induced Oxidative α‐keto‐Dichlorination of Arylalkynes by CuCl 2 at Room Temperature . ChemSusChem 15:17.
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Marre Porré, Gianmarco Pisanò, Fady Nahra & Catherine S. J. Cazin. (2022) Synthetic Access to Aromatic α-Haloketones. Molecules 27:11, pages 3583.
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Pratiksha P. Gawas, Buthanapalli Ramakrishna, N. Veeraiah & Venkatramaiah Nutalapati. (2021) Multifunctional hydantoins: recent advances in optoelectronics and medicinal drugs from Academia to the chemical industry. Journal of Materials Chemistry C 9:46, pages 16341-16377.
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Richard C. LarockRichard C. Larock & Li Zhang. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 62 .
Shi‐Zhong Tang, Wenshuang Zhao, Tao Chen, Yang Liu, Xiao‐Ming Zhang & Fu‐Min Zhang. (2017) A Simple and Efficient Method for the Preparation of α‐Halogenated Ketones Using Iron(III) Chloride and Iron(III) Bromide as Halogen Sources with Phenyliodonium Diacetate as Oxidant. Advanced Synthesis & Catalysis 359:23, pages 4177-4183.
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Gregory L. Beutner, Jacob Albrecht, Junying Fan, Dayne Fanfair, Michael J. Lawler, Michael Bultman, Ke Chen, Sabrina Ivy, Richard L. Schild, Jonathan C. Tripp, Saravanababu Murugesan, Konstantinos Dambalas, Douglas D. McLeod, Jason T. Sweeney, Martin D. Eastgate & David A. Conlon. (2017) Preparation of the HIV Attachment Inhibitor BMS-663068. Part 3. Mechanistic Studies Enable a Scale-Independent Friedel–Crafts Acylation. Organic Process Research & Development 21:8, pages 1122-1130.
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Ming Zeng, Rui-Xue Huang, Wen-Yi Li, Xiao-Wen Liu, Fu-Ling He, Yi-Yuan Zhang & Fang Xiao. (2016) In(OTf) 3 /acid co-catalyzed hydration of 1-haloalkynes to α-halomethyl ketones. Tetrahedron 72:27-28, pages 3818-3822.
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Sarita Khandelwal, Yogesh Kumar Tailor & Mahendra Kumar. (2016) Deep eutectic solvents (DESs) as eco-friendly and sustainable solvent/catalyst systems in organic transformations. Journal of Molecular Liquids 215, pages 345-386.
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Masoud Sadeghi, Javad Safari & Zohre Zarnegar. (2016) Synthesis of 2-aminothiazoles from methylcarbonyl compounds using a Fe 3 O 4 nanoparticle-N-halo reagent catalytic system . RSC Advances 6:69, pages 64749-64755.
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Ardeshir Khazaei, Fatemeh Abbasi, Ahmad Reza Moosavi‐Zare, Marzieh Khazaei & M. Hassan Beyzavi. (2015) Condensation of Aryl Aldehydes, 2‐naphthol, and Thioacetamide Catalyzed by N ‐halo Reagents in Neutral Media . Journal of the Chinese Chemical Society 62:10, pages 850-854.
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Abhaya K. Mishra, Honnappa Nagarajaiah & Jarugu Narasimha Moorthy. (2015) Trihaloisocyanuric Acids as Atom‐Economic Reagents for Halogenation of Aromatics and Carbonyl Compounds in the Solid State by Ball Milling. European Journal of Organic Chemistry 2015:12, pages 2733-2738.
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Rok Prebil & Stojan Stavber. (2014) The α‐Chlorination of Aryl Methyl Ketones under Aerobic Oxidative Conditions. Advanced Synthesis & Catalysis 356:6, pages 1266-1274.
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Zheng-Wang Chen, Dong-Nai Ye, Min Ye, Zhong-Gao Zhou, Shen-Huan Li & Liang-Xian Liu. (2014) AgF/TFA-promoted highly efficient synthesis of α-haloketones from haloalkynes. Tetrahedron Letters 55:7, pages 1373-1375.
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Ardeshir Khazaei, Fatemeh Abbasi & Ahmad Reza Moosavi-Zare. (2014) Efficient preparation of some new 1-carbamato-alkyl-2-naphthols using N-halo reagents in neutral media. RSC Adv. 4:3, pages 1388-1392.
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Zhou Zhong-shi, Li Li & He Xue-han. (2019) A One-Pot Method Synthesis of α-Chloroketone Dimethyl Acetals. Journal of Chemical Research 37:10, pages 633-635.
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Zhong Shi Zhou, Li Li & Xue Han He. (2012) A simple and convenient method for direct α-chlorination of ketones with ammonium chloride and Oxone®. Chinese Chemical Letters 23:11, pages 1213-1216.
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Peraka Swamy, Macharla Arun Kumar, Marri Mahender Reddy & Nama Narender. (2012) Mild and Efficient α-Chlorination of Carbonyl Compounds Using Ammonium Chloride and Oxone (2KHSO5·KHSO4·K2SO4). Chemistry Letters 41:4, pages 432-434.
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Tarek A. Salama & Zoltán Novák. (2011) N-Halosuccinimide/SiCl4 as general, mild and efficient systems for the α-monohalogenation of carbonyl compounds and for benzylic halogenation. Tetrahedron Letters 52:31, pages 4026-4029.
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Robert MartinRobert Martin. 2011. Aromatic Hydroxyketones: Preparation and Physical Properties. Aromatic Hydroxyketones: Preparation and Physical Properties 1649 1733 .
Seyedeh Fatemeh Hojati, Mostafa Gholizadeh, Mahnaz Haghdoust & Fatemeh Shafiezadeh. (2010) 1,3-Dichloro-5,5-dimethylhydantoin as a Novel and Efficient Homogeneous Catalyst in Biginelli Reaction. Bulletin of the Korean Chemical Society 31:11, pages 3238-3240.
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Daniel C. Whitehead, Richard J. Staples & Babak Borhan. (2009) A simple and expedient method for the preparation of N-chlorohydantoins. Tetrahedron Letters 50:6, pages 656-658.
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Zizhan Chen, Bin Zhou, Huihua Cai, Wei Zhu & Xinzhuo Zou. (2009) Simple and efficient methods for selective preparation of α-mono or α,α-dichloro ketones and β-ketoesters by using DCDMH. Green Chem. 11:2, pages 275-278.
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Ram N. Ram & T. P. Manoj. (2008) Copper(I)-Promoted Synthesis of Chloromethyl Ketones from Trichloromethyl Carbinols. The Journal of Organic Chemistry 73:14, pages 5633-5635.
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Zijin Xu, Deyan Zhang & Xinzhuo Zou. (2006) α‐Chlorination of Acetophenones Using 1,3‐Dichloro‐5,5‐dimethylhydantoin.. ChemInform 37:23.
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