Synthesis of 3-Hydroperoxy (or Hydroxy)-substituted 1,2-Dioxanes and 1,2-Dioxepanes by the Ozonolysis of Unsaturated Hydroperoxy Acetals

Abstract

Mono-ozonolysis of dienes in methanol gave in each case the corresponding unsaturated hydroperoxy acetals.The reaction of the hydroperoxides with ozone in the solvent system such as AcOH-CH 2 Cl 2 resulted in the production of the corresponding hydroperoxy (or hydroxy)substituted 1,2-dioxanes or 1,2-dioxepanes in good yield.By the treatment of the derived products with TMSOTf-Et 3 SiH, replacement of the methoxy (or hydroxy) group by hydrogen was accomplished.