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 journalArticle

21 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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  • Cite this

    Kirihara, M., Kakuda, H., Ichinose, M., Ochiai, Y., Takizawa, S., Mokuya, A., Okubo, K., Hatano, A., & Shiro, M. (2005). Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate. Tetrahedron, 61(20), 4831-4839. https://doi.org/10.1016/j.tet.2005.03.033