Tetrahedron

Synthesis and photosensitized oxygenation of cyclopropylidenecyclobutenes

O Sharon, AA Frimer

Index: Sharon, Ofer; Frimer, Aryeh A. Tetrahedron, 2003 , vol. 59, # 41 p. 8153 - 8162

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Citation Number: 11

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 1O2, via an 'ene'process, initially generating a cyclopropyl hydroperoxide, which proceeds ...