1,2,3-Triols: Partial Oxidation of γ-Silyl Allylic Alcohols with Ozone

Significance

In a unique oxidation of an alkene with ozone, the vinylsilane moiety does not undergo the normal cleavage of the double bond. The solvent is the key to the unusual reaction since a 1:1 mixture of 2:(usual ozonolyzed product) was observed in CH₂Cl₂. The reaction is chemoselective since an alkene was oxidized in presence of an alkyne group. The authors noted that the silyl peroxides are stable and require no special handling (slow degradation above 80 °C).