Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate

Masayuki Kirihara, Hiroko Kakuda, Motohiro Ichinose, Yuta Ochiai, Shinobu Takizawa, Asuka Mokuya, Kumiko Okubo, Akihiko Hatano, Motoo Shiro

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

Tertiary cyclopropanol compounds react with a catalytic amount of vanadyl acetylacetonate in the presence of oxygen affording β-hydroxyketones and β-diketones. For 3-substituted-bicyclo[4.1.0]alkanols, peroxides are obtained, as are the β-hydroxyketones. Conversely, 2- ethoxycarbonylcyclopropyl silyl ethers produce ethyl γ-oxocarboxylate derivatives given the same reaction conditions.

Original languageEnglish
Pages (from-to)4831-4839
Number of pages9
JournalTetrahedron
Volume61
Issue number20
DOIs
Publication statusPublished - 2005 May 16
Externally publishedYes

Keywords

  • Cyclopropanes
  • Fragmentation reactions
  • Peroxides
  • Vanadium compounds

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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