33657-50-0Relevant articles and documents
Solvent-free preparation of α,α-dichloroketones with sulfuryl chloride
Tu, Dewei,Luo, Juan,Jiang, Wengao,Tang, Qiang
supporting information, (2021/09/15)
An efficient and facile method is reported for the synthesis of a series of α,α-dichloroketones. The direct dichlorination of methyl ketones and 1,3-dicarbonyls using an excess amount of sulfuryl chloride affords the corresponding gem-dichloro compounds in moderate to excellent yields. Moreover, the protocol features high yields, broad substrate scope, and simple reaction conditions without using any catalysts and solvents.
Dichlorination of α-Diazo-β-dicarbonyls using (dichloroiodo)benzene
Coffey, Keith E.,Murphy, Graham K.
supporting information, p. 1003 - 1007 (2015/05/20)
Abstract α-Diazo-β-dicarbonyl compounds were chlorinated using (dichloro)iodobenzene and an activating catalyst. A broad range of reaction rates was observed, which paralleled the relative stability/nucleo-philicity of the diazo compounds. Acyclic diazocarbonyls reacted faster than cyclics, and β-diketones were much faster to react than β-keto esters or β-diesters. Lewis acid activation was used for the first time, allowing us to overcome instances of poor chemoselectivity. Though the yields ranged from low to good, this chlorination reaction has again proven a mild and effective halogenation strategy.
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.
CHLORINATION OF ACETYLACETONE AND ACETOACETIC AND MALONIC ESTERS.
Amriev,Velichko,Abdulkina
, p. 2318 - 2322 (2007/10/02)
To develop a laboratory procedure for the one-stage chlorination of ME, AAcE, and AA, the authors studied the action of gaseous chlorine on these compounds. We found that when the chlorination is carried out at 55-60 degree C, the formation of side products is reduced to a minimum. The reaction begins at 35-40 degree C, and then proceeds exothermally, and it can be easily controlled by external cooling or by decrease in the rate of chlorine input. The optimal reaction regime lies within 55-60 degree C. Further increase in temperature leads to the formation of trichloro derivatives and more extensive chlorination. If the chlorination reaction is carried out for 7-8 h at 55-60 degree C, dichloro derivatives of ME, AAcE, and AA are mainly formed, and the yields in the most favorable experiments are equal to (%): DCM 93, DCAAc 87, DCAA 75. Under these conditions, only inappreciable amounts of monochloro derivatives and more extensively chlorinated products are present in the reaction mixture. The authors isolated mono-, di-, and trichloro derivatives of ME, AAcE and AA.
Reaction of 1,3-Dicarbonyl Compounds with Nitryl Chloride
Prostenik, Mladen V.,Dumic, Miljenko,Bosnjak, Nada
, p. 771 - 774 (2007/10/02)
Reaction of 1,3-dicarbonyl compounds with nitryl chloride through substitution on the activated methylene group, resulted in the formation of chloro, dichloro and oximino derivatives. - Keywords: 3-Oxobutanoic acid ethyl ester; 2,4-Petanedione; reaction with nitryl chloride
