THE PHOTOOXYGENATION OF OLEFINS AND THE ROLE OF ZWITTERIONIC PEROXIDES

The article describes how olefins, particularly bridged bicyclic ones, react with singlet oxygen to give initially zwitterionic peroxides. Evidence (or these fugitive species is obtained by trapping with alcohols and aldehydes. In the case of electron-rich mono-olefins, photo-oxygenation in the presence of aldehydes leads to 1,2,4-trioxanes and provides the mechanistic basis for a new methodology for preparing this hitherto unknown class of saturated oxygen heterocycles, certain members of which have potential as anti-parasitic agents.