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UBC Theses and Dissertations

Synthetic applications of dishcargegenerated singlet oxygen Ouchi, M. Dennis,

Abstract

The electric discharge method of generating, singlet-molecular oxygen was demonstrated to be a useful technique for preparative scale oxygenations of suitable organic substrates. Representative examples of known singlet oxygen acceptors were exposed to discharge-generated singlet oxygen while dissolved in organic solvents at -78⁰ or adsorbed onto solid supports at room temperature. Typical oxygenation products were obtained in generally good yields. The various known methods of generating singlet molecular oxygen and the relative advantages and disadvantages of the electric discharge method are-discussed. Adsorption of substrates onto solid surfaces appears to have no effect on the course of the addition of singlet oxygen to the organic moiety. The success of this technique is perhaps due to the increase in the surface area of contact between the substrate and singlet oxygen.. Exploratory oxygenations of l,⁴-dienes and epoxides adsorbed onto solid surfaces were all unsuccessful.

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