Cycloadditions. 24. Addition of Dichloroketene To Silyl Enol Ethers. Synthesis of Functionalized Cyclobutanones

Larry R. Krepski, Alfred Hassner

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

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 elimination to generate a dichlorocyclobutenone was observed. The silyl enol ethers derived from acetophenone and pinacolone, on the other hand, afforded only acyclic products from the dichloroketene. The possibility that these acyclic products may result from ring opening of initially formed cyclobutanones is discussed.

Original languageEnglish
Pages (from-to)3173-3179
Number of pages7
JournalJournal of Organic Chemistry
Volume43
Issue number16
DOIs
StatePublished - 1978
Externally publishedYes

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