Abstract
[reaction: see text] 1-Substituted 1-(2,2-diphenylvinyl)cyclopropanes with electron-accepting groups at C1 undergo a novel rearrangement to benzocycloheptenes on triplet-sensitized irradiation. In some instances competition between rearrangement to cyclopentenes and formation of cycloheptenes takes place. When electron-acceptor groups are not present at C1, conventional ring opening to cyclopentenes occurs exclusively. A mechanism involving intramolecular SET from the diphenylvinyl unit to the electron-acceptor group is proposed for this novel photoreaction.
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