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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 1
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Original Articles

α-Chlorination of Ketones with Sodium Chlorite, Mn(acac)3, and Alumina in Dichloromethane

Shigetaka Yakabe Department of Applied Chemistry, Faculty of Technology, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184, Japan
,
Masao Hirano Department of Applied Chemistry, Faculty of Technology, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184, Japan
&
Takashi Morimoto Department of Applied Chemistry, Faculty of Technology, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184, Japan
Pages 131-138 | Received 01 Jul 1997, Published online: 20 Aug 2006

Citations (18)

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A. Paul Krapcho. (2006) USES OF SODIUM CHLORITE AND SODIUM BROMATE IN ORGANIC SYNTHESIS. A REVIEW. Organic Preparations and Procedures International 38:2, pages 177-216.
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Articles from other publishers (17)

Jia-Chen Xiang, Jia-Wei Wang, Peng Yuan, Jin-Tian Ma, An-Xin Wu & Zhi-Xin Liao. (2022) Switching Over of the Chemoselectivity: I 2 -DMSO-Enabled α,α-Dichlorination of Functionalized Methyl Ketones . The Journal of Organic Chemistry 87:22, pages 15101-15113.
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Zhihui Wang, Lei Wang, Zhiming Wang, Pinhua Li & Yicheng Zhang. (2021) A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions. Chinese Chemical Letters 32:1, pages 429-432.
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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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L. L. Frolova, A. V. Popov, L. V. Bezuglaya, I. N. Alekseev, P. A. Slepukhin & A. V. Kutchin. (2016) Reactions of terpene alcohols and diols with chlorine dioxide in dimethylformamide. Russian Journal of General Chemistry 86:3, pages 613-621.
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Carlos G. Gómez-Fosado, Leticia Quintero, Lilia Fuentes & Fernando Sartillo-Piscil. (2015) The use of sodium chlorite in the non-racemic synthesis of a potent inhibitor of glycolipid biosynthesis. Tetrahedron Letters 56:41, pages 5607-5609.
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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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Pranjal Gogoi, Pranjal Bezboruah, Junali Gogoi & Romesh C. Boruah. (2013) ipso -Hydroxylation of Arylboronic Acids and Boronate Esters by Using Sodium Chlorite as an Oxidant in Water . European Journal of Organic Chemistry 2013:32, pages 7291-7294.
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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 (2KHSO 5 ·KHSO 4 ·K 2 SO 4 ) . Chemistry Letters 41:4, pages 432-434.
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Weimin He, Longyong Xie, Yingying Xu, Jiannan Xiang & Liming Zhang. (2012) Electrophilicity of α-oxo gold carbene intermediates: halogen abstractions from halogenated solvents leading to the formation of chloro/bromomethyl ketones. Organic & Biomolecular Chemistry 10:16, pages 3168.
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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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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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Xing Hai Li, Xin Ling Yang, Xiao Mei Liang, Zhen Peng Kai, Yun Ling, Fu Heng Chen & Dao Quan Wang. (2007) A new approach to the synthesis of α-chlorocycloalkanones. Chinese Chemical Letters 18:12, pages 1476-1478.
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Mitsuhiro Yoshimatsu, Miho Sakai & Eri Moriura. (2007) Novel Building Blocks: 1-Aryl-2-chloro-1-ethoxyethenes – Preparations and Transformations. European Journal of Organic Chemistry 2007:3, pages 498-507.
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V. Caprio. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 135 214 .
Michael B. Smith. 2002. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 238 348 .
S. YAKABE, M. HIRANO & T. MORIMOTO. (2010) ChemInform Abstract: α-Chlorination of Ketones with Sodium Chlorite, Mn(acac)3, and Alumina in Dichloromethane.. ChemInform 29:21, pages no-no.
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