Medium-Ring Systems. 5.1 Synthesis and Base-Catalyzed Isomerizations of Medium-Ring Cycloalkenones with Electron-Withdrawing Substituents

Ronnie C. Mease, Jerry A. Hirsch

Research output: Contribution to journalArticle

Abstract

Medium-ring 3-cycloalkenones with electron-withdrawing substituents at the 3-position have been synthesized and subjected to base-catalyzed isomerizations. In a given ring size in the seven-and eight-membered carbocycles, the substituents studied caused similar shifts in the equilibria toward the 3-cycloalkenones relative to the unsubstituted cases. Steric effects of the substituents are therefore not significant. As the ring size is increased, the preference for the 3-cycloalkenone becomes more pronounced. In the nine-and ten-membered systems, an additional equilibrium involving formation of 4-cycloalkenones appears. Decreased effectiveness of conjugative interactions in endocyclic dienolates and in 2-cycloalkenones with increasing ring size is suggested.

Original languageEnglish (US)
Pages (from-to)2925-2937
Number of pages13
JournalJournal of Organic Chemistry
Volume49
Issue number16
DOIs
StatePublished - Feb 1984
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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