Trimethylsilyl group migrations in cryogenic ozonolysis of trimethylsilylethene: evidence for nonconcerted primary ozonide decomposition pathway

R Fajgar; J Roithová; J Pola

doi:10.1021/jo010340i

Trimethylsilyl group migrations in cryogenic ozonolysis of trimethylsilylethene: evidence for nonconcerted primary ozonide decomposition pathway

J Org Chem. 2001 Oct 19;66(21):6977-81. doi: 10.1021/jo010340i.

Authors

R Fajgar¹, J Roithová, J Pola

Affiliation

¹ Institute of Chemical Process Fundamentals, Academy of Sciences of the Czech Republic, 165 02 Prague, Czech Republic.

PMID: 11597216
DOI: 10.1021/jo010340i

Abstract

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.