Synthetic Communications

New, Efficient Synthesis of α-Chloroketones Using SiCl4/Urea–Hydrogen Peroxide or SiCl4/Iodosylbenzene Reagent Systems

AAS El-Ahl, AH Elbeheery, FA Amer

Index: El-Ahl, Abdel Aziz S.; Elbeheery, Akram H.; Amer, Fathy A. Synthetic Communications, 2011 , vol. 41, # 10 p. 1508 - 1513

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Citation Number: 6

Abstract

Abstract Alkyl aryl ketones on treatment with SiCl4/urea–hydrogen peroxide (UHP) or SiCl4/iodosylbenzne reagent systems afforded α-chloroketones in excllent yields, while ketones with higher enol content provide exclusively α, α-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 ...