Criegee proposed that the ozonolysis mechanism proceeds by means of a [3+2] cycloaddition, forming a carbonyl oxide and a carbonyl. This carbonyl oxide then recombines with the carbonyl, or a dipolarophile. Kuczkowski investigated the ozonolysis of vinyl ethers and found that recombination of the carbonyl oxide and the vinyl ether was observed. We are investigating a way to produce a carbonyl oxide and disconnect it from ozone to react with a dipolarophile by a [3+2] cycloaddition. Currently the synthesis of vinyl peroxidic enols which can tautomerize to carbonyl oxides are being attempted.
Weaver, M. G. (2010). Progress Towards the Synthesis of Stabilized Carbonyl Oxides (Undergraduate honors thesis, University of Redlands). Retrieved from http://inspire.redlands.edu/cas_honors/55