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Paper | Regular issue | Vol 53, No. 6, 2000, pp.1293-1304
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8874
Synthesis of 3-Hydroperoxy (or Hydroxy)-substituted 1,2-Dioxanes and 1,2-Dioxepanes by the Ozonolysis of Unsaturated Hydroperoxy Acetals

Takahiro Tokuyasu, Toyonari Ito, Araki Masuyama, and Masatomo Nojima*

*Department of Materials Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan

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-CH2Cl2 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-Et3SiH, replacement of the methoxy (or hydroxy) group by hydrogen was accomplished.