Allylic Displacements and a Novel Ester-Ether Interchange in Fused Cyclobutanones

Alfred Hassner, John Dillon

Research output: Contribution to journalArticlepeer-review

22 Scopus citations


Chlorophenylcyclobutanone 11, prepared by chlorophenylketene addition to cyclohexene, reacts readily with simple and hindered carboxylic acids in a cine substitution to produce keto esters 14. The acyloxy and phenyl substituents in 14c are shown by X-ray diffraction to be cis oriented; nevertheless 14 reacts with NaOMe at 20 °C by an unusual ester-ether interchange to produce 15 and the released carboxylate RCO2-. These reactions apparently proceed via an oxyallyl cation intermediate. The behaviors of related cyclobutanones 4, 6, and 11 with methoxide are contrasted.

Original languageEnglish
Pages (from-to)3315-3319
Number of pages5
JournalJournal of Organic Chemistry
Issue number17
StatePublished - 1986
Externally publishedYes


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