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

19 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

Fingerprint

Ethyl Ethers
Peroxides
Oxygen
Derivatives
cyclopropanol
acetyl acetonate

Keywords

  • Cyclopropanes
  • Fragmentation reactions
  • Peroxides
  • Vanadium compounds

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Kirihara, M., Kakuda, H., Ichinose, M., Ochiai, Y., Takizawa, S., Mokuya, 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

Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate. / Kirihara, Masayuki; Kakuda, Hiroko; Ichinose, Motohiro; Ochiai, Yuta; Takizawa, Shinobu; Mokuya, Asuka; Okubo, Kumiko; Hatano, Akihiko; Shiro, Motoo.

In: Tetrahedron, Vol. 61, No. 20, 16.05.2005, p. 4831-4839.

Research output: Contribution to journalArticle

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, vol. 61, no. 20, pp. 4831-4839. https://doi.org/10.1016/j.tet.2005.03.033
Kirihara M, Kakuda H, Ichinose M, Ochiai Y, Takizawa S, Mokuya A et al. Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate. Tetrahedron. 2005 May 16;61(20):4831-4839. https://doi.org/10.1016/j.tet.2005.03.033
Kirihara, Masayuki ; Kakuda, Hiroko ; Ichinose, Motohiro ; Ochiai, Yuta ; Takizawa, Shinobu ; Mokuya, Asuka ; Okubo, Kumiko ; Hatano, Akihiko ; Shiro, Motoo. / Fragmentation of tertiary cyclopropanol compounds catalyzed by vanadyl acetylacetonate. In: Tetrahedron. 2005 ; Vol. 61, No. 20. pp. 4831-4839.
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