Synthesis of Hydroxy(or Hydroperoxy)-Substituted 1,2,4-Trioxacycloalkanes by the Ozonolysis of Unsaturated Hydroperoxy Acetals

Ozonolyses of unsaturated hydroperoxy acetals 4a−k gave in each case the mixtures of products containing the corresponding trioxanes 8a−f and 12e,f, trioxepanes 12g−i, trioxocane 12j, and trioxonane 12k. By choosing the proper conditions of the ozonolysis, the desired cyclic peroxide was selectively...

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Bibliographic Details
Published in:Journal of organic chemistry 1997-07, Vol.62 (15), p.4949-4954
Main Authors: Ushigoe, Yoshihiro, Torao, Yuko, Masuyama, Araki, Nojima, Masatomo
Format: Article
Language:English
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Summary:Ozonolyses of unsaturated hydroperoxy acetals 4a−k gave in each case the mixtures of products containing the corresponding trioxanes 8a−f and 12e,f, trioxepanes 12g−i, trioxocane 12j, and trioxonane 12k. By choosing the proper conditions of the ozonolysis, the desired cyclic peroxide was selectively obtained in moderate to good yield. Alternatively, acid-catalyzed cyclization of the methanol-derived ozonolysis products 13h and 13j provided the corresponding trioxepane 12h and trioxocane 12j, respectively.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo970555l