Cyclopentanones from Nucleophilic Addition/Carbonylation to (η4-Diene)Fe(CO)3 Complexes

Martin F. Semmelhack, James W. Herndon, John K. Llu1b

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

The addition of carbon nucleophiles to (1,3-diene)lron tricarbonyl complexes produces (homoallyl)Fe-(CO)3 anionic complexes; as reported earlier, CO is incorporated at 1.5 atm to give acyliron anionic complexes. With most open-chain 1,3-diene ligands, further cyclization occurs, producing cyclopentanone derivatives with the anionic substituent in the 3-position. The yields are good if the nucleophiles are sufficiently reactive, while the primary limitation is the resistance to ring closure with multiply substituted dienes. With 2-substituted 1,3-dienes, the cyclopentanone product is formed with a specific cis relationship of the substitutents at C-3 and C-4. Through deuterium labeling studies, a mechanism involving β-hydride elimination/readdition is demonstrated as the final stage of the cyclopentanone formation.

Original languageEnglish (US)
Pages (from-to)1885-1888
Number of pages4
JournalOrganometallics
Volume2
Issue number12
DOIs
StatePublished - Jan 1 1983

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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