The Journal of Organic Chemistry

Cycloadditions. 24. Addition of dichloroketene to silyl enol ethers. Synthesis of functionalized cyclobutanones

LR Krepski, A Hassner

Index: Krepski,L.R.; Hassner,A. Journal of Organic Chemistry, 1978 , vol. 43, p. 3173 - 3179

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Citation Number: 38

Abstract

Dichloroketene, generated from trichloroacetyl chloride and activated zinc, has been found to react readily with silyl enol ethers. In most cases, good yields of 3-siloxy-substituted dichlorocyclobutanones could be isolated. The reaction appears to be both regio-and stereospecific. Mild acid hydrolysis of the siloxycyclobutanones afforded the corresponding 3-hydroxydichlorocyclobutanones. In some cases, cyclobutane ring opening or ...