31315-51-2Relevant academic research and scientific papers
Electrochemical Oxidative Oxydihalogenation of Alkynes for the Synthesis of α,α-Dihaloketones
Meng, Xiangtai,Zhang, Yu,Luo, Jinyue,Wang, Fei,Cao, Xiaoji,Huang, Shenlin
supporting information, p. 1169 - 1174 (2020/02/04)
An electrochemical oxydihalogenation of alkynes has been developed for the first time. Using this sustainable protocol, a variety of α,α-dihaloketones can be prepared with readily available CHCl3, CH2Cl2, ClCH2CH2Cl, and CH2Br2 as the halogen source under electrochemical conditions at room temperature.
Synthesis of α,α-Dichloroketones through Sequential Reaction of Decarboxylative Coupling and Chlorination
Cho, Eunjeong,Kim, Myungjin,Jayaraman, Aravindan,Kim, Jimin,Lee, Sunwoo
supporting information, p. 781 - 784 (2018/02/21)
2,2-Dichloro-1,2-diarylethanones were synthesized from diarylalkynes and trichloroisocyanuric acid. The reaction was conducted in CH3CN/H2O at room temperature for 12 h. In addition, the desired 2,2-dichloro-1,2-diarylethanones could be prepared from aryl bromides and propiolic acid through sequential Pd-catalyzed decarboxylative coupling and chlorination. This method showed moderate to good yields and good tolerance toward functional groups such as chlorides, bromides, aldehydes, and ketones.
Practical approach for preparation of unsymmetric benzils from β-ketoaldehydes
Ruan, Libo,Shi, Min,Li, Nian,Ding, Xu,Yang, Fan,Tang, Jie
, p. 733 - 735 (2014/03/21)
An efficient and practical method for the synthesis of unsymmetric benzils from readily available β-ketoaldehydes has been developed. Various unsymmetric 1,2-diaryldiketones bearing functional groups have been obtained in good to excellent yields under mild reaction conditions. A plausible mechanism was proposed, and α,α-dichloroketone was considered as the key intermediate. The generation of α,α-dichloroketones from β-ketoaldehydes may undergo the following steps: (1) oxidation by sodium hypochlorite, (2) decarboxylation, and (3) chlorination by Cl2 generated from sodium hypochlorite.
New, efficient synthesis of α-chloroketones using SiCl 4/urea-hydrogen peroxide or SiCl4/iodosylbenzene reagent systems
El-Ahl, Abdel Aziz S.,Elbeheery, Akram H.,Amer, Fathy A.
experimental part, p. 1508 - 1513 (2011/06/17)
Alkyl aryl ketones on treatment with SiCl4/urea-hydrogen peroxide (UHP) or SiCl4/iodosylbenzne reagent systems afforded -chloroketones in excllent yields, while ketones with higher enol content provide exclusively,-dichloroketones under exceedingly mild conditions. The reaction proceeds via the initial formation of silyl enol ethers. A polarized chlorine intermediate that resulted from the coordination of SiCl4 with the in situ formed trichlorosilyl hypochlorite Cl3SiOCl is thought to be the active chlorinating agent.
A convenient and practical approach to α-diketones via reactions of internal aryl alkynes with N-iodosuccinimide/water
Niu, Mingyu,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
scheme or table, p. 2879 - 2882 (2009/04/06)
A convenient and practical approach to α-diketones via reactions of alkynes with N-iodosuccinimides/water at 70°C has been developed. Georg Thieme Verlag Stuttgart.
Selective preparation of α,α-dichloroketones with copper(II) chloride
Nobrega, Jose Arimateia,Goncalves, Simone Maria C.,Peppe, Clovis
, p. 3711 - 3717 (2007/10/03)
Aryl and enolizable alkyl ketones react with copper(II) chloride in dimethylformamide to produce the corresponding α,α-dichloroketone in high yields. Remarkable qualities of the process are high selectivity towards these substrates, undetected polychlorinated by-products, easy work-up, commercially available reagents and HCl as the only waste stream.
Reaction of α,β-Unsaturated Carboxylic Acids with Manganese(III) Acetate in the Presence of Chloride Ion
Yonemura, Hiroshi,Nishino, Hiroshi,Kurosawa, Kazu
, p. 3153 - 3160 (2007/10/02)
The reaction of 3-phenylpropenoic acids with manganese(III) acetate - Cl- complex yielded 1,2,2-trichloro-1-phenylethanes, 1-acetoxy-2,2-dichloro-1-phenylethanes, and 2,2-dichloro-1-phenylethanols. (E)-2,3-Diphenylpropenoic acids gave 2,2-dichloro-1,2-diphenylethanones and 2-acetoxy-1,2-diphenylethanones. 3,3-Diphenylpropenoic acids yielded 2,2-dichloro-1,1-diphenylethenes, 1-acetoxy-2,2-dichloro-1,1-diphenylethanes, 2,2-dichloro-1,1-diphenyl-1-ethanols, and 2-hydroxy-2,2-diphenylethanal.Fluorenylideneacetic acid gave 9-chloro-9-(dichloromethyl)fluorene, 9-acetoxy-9-(dichloromethyl)fluorene, and 9-fluorenone. 1-Cyclohexenecarboxylic acid yielded 1,2-dichlorocyclohexanecarboxylic acid and 1-acetoxy-2-chlorocyclohexanecarboxylic acid.The reaction can be explained in terms of a free-radical mechanism involving manganese(III) acetate - Cl- complexation, addition of Cl. radical, decarboxylation, and the oxidation of chloroethenes which are the reaction intermediates.
The α-Chlorination of Aryl Ketones with Manganese(III) Acetate in the presence of Chloride Ion
Tsuruta, Takehiko,Harada, Tetsuya,Nishino, Hiroshi,Kurosawa, Kazu
, p. 142 - 145 (2007/10/02)
The reaction of 2-(4-methoxyphenyl)-4-chromanone with Mn(OAc)3 in the presence of LiCl gave 3,3-dichloro-2-(4-methoxyphenyl)-4-chromanone.The reactions of 2-phenyl-4-chromanone, 1-phenyl-1-propanone, 1,2-diphenylethanone, and 1-tetralone similarly yielded α,α-dichloro derivatives in good yields. 2,2,2-Trichloroacetophenones were obtained from 2,2-dichloroacetophenones, but in the absence of LiCl, 2,2-dichloroacetophenones gave 2,2,3,3-tetrachloro-1,4-butanediones.KCl, NaCl, NH4Cl,AlCl3, and CaCl2 were also employed as the Cl- ion source.Synthetic applicability and the reaction mechanisms are discussed briefly.
