Journal
SYNTHETIC COMMUNICATIONS
Volume 41, Issue 10, Pages 1508-1513Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2010.487173
Keywords
-Chloroketones; iodosylbenzene; silyl peroxides; tetrachlorosilane (TCS); urea-hydrogen peroxide (UHP)
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[image omitted] 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.
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