Criegee Intermediates Beyond Ozonolysis: Synthetic and Mechanistic Insights

Abstract

After more than 70 years since their discovery, Criegee intermediates (CIs) are back at the forefront of modern chemistry of short-lived reactive intermediates. They play an important role in the mechanistic context of chemical synthesis, total synthesis, pharmaceuticals, and, most importantly, climate-controlling aerosol formation as well as atmospheric chemistry. This Minireview summarizes key aspects of CIs (from the mechanism of formation, for example, by ozonolysis of alkenes and photolysis methods employing diiodo and diazo compounds, to their electronic structures and chemical reactivity), highlights the most recent findings and some landmark results of gas-phase kinetics, and detection/measurements. The recent progress in synthetic and mechanistic studies in the chemistry of CIs provides a guide to illustrate the possibilities for further investigations in this exciting field.

Keywords: 1,3-dipolar cycloadditions; Criegee intermediates; atmospheric chemistry; carbonyl oxides; ozonolysis.