Photosensitized Oxygenation of Olefins with Zinc Tetraphenylporphine-1,4-Diazabicyclooctane Complex

Article abstract of DOI:10.1246/bcsj.65.1944

In the presence of a proper amount of amines such as 1,4-diazabicyclo<2.2.2>octane (DABCO) and piperidine, zinc tetraphenylporphine (ZnTPP) works as a not only apparently more effective but also more photoresistant sensitizer for singlet-oxygen oxygenation of olefins than in the absence of the amines.This is ascribed to the facts that ZnTPP forms a 1:1 complex with DABCO, and that DABCO coordinated to ZnTPP has no ability to quench singlet oxygen, as revealed by detection of singlet oxygen phosphorescence and product distributions in oxygenation of d-limonene, 1,2-dimethylcyclohexene, and 1-phenylcyclobutene.