Synthesis and photosensitized oxygenation of cyclopropylidenecyclobutenes

Ofer Sharon, Aryeh A. Frimer

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Cyclopropylidenecyclobutenes and -cyclobutanes were conveniently prepared using the Petasis titanocene approach. The cyclobutenes were unreactive to singlet oxygen, reacting sluggishly via a photoinitiated free radical autooxidative epoxidation process, to yield the corresponding spiroketones. By contrast, cyclopropylidenecyclobutanes react rapidly with 1O 2, via an 'ene' process, initially generating a cyclopropyl hydroperoxide, which proceeds to products via Hock cleavage. The inertness of cyclopropylidenecyclobutenes to a 1O2 'ene' reaction mode may be attributed to the fact that it would require the formation of the relatively high energy cyclobutadiene moiety.

Original languageEnglish
Pages (from-to)8153-8162
Number of pages10
JournalTetrahedron
Volume59
Issue number41
DOIs
StatePublished - 6 Oct 2003

Keywords

  • Autoxidation
  • Cyclopropylidenecyclobutanes
  • Cyclopropylidenecyclobutenes
  • Epoxidation
  • Oxygen
  • Singlet
  • Synthesis

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