Trimethylsilyl Group Migrations in Cryogenic Ozonolysis of Trimethylsilylethene: Evidence for Nonconcerted Primary Ozonide Decomposition Pathway

The identification of trimethylsiloxy-1,2-dioxetane and 2-trimethylsilyloperoxyacetaldehyde and assignment of trimethylsiloxymethyl formate as products of the low-temperature ozonolysis of trimethylsilylethene demonstrate feasibility of migrations of trimethylsilyl group in a dioxygen-centered (oxyperoxy) diradical produced via a homolytic cleavage of each of both O-O bonds in the primary ozonide. The results provide the first experimental evidence on the nonconcerted decomposition of the primary ozonide.