Novel aspects of carbonyl oxide chemistry

The structural and chemical properties of 1,3-dipolar peroxidic species (X—O—O) such as ozone (X=O) and carbonyl oxides (X=R2C) depend significantly on the nature of X. Although cyclic O3 is thermodynamically unstable, dioxiranes, cyclic isomers of carbonyl oxides, are isolable and have been fully characterized. In contrast to the well known electrophilic nature of ozone, carbonyl oxides usually act as a nucleophilic oxygen transfer agent, but their reactivity could be altered by substituents. It is expected that the chemistry of R2C—O2 species will provide a good starting point for a better understanding of dioxygen complexes (X—O2) with various Xs. Interesting aspects of carbonyl oxide chemistry are discussed, including methods of generation, cyclization to dioxiranes and the nature of their oxygen transfer activities. © 1997 John Wiley & Sons, Ltd.