Synthesis of Hydroxy(or Hydroperoxy)-Substituted 1,2,4-Trioxacycloalkanes by the Ozonolysis of Unsaturated Hydroperoxy Acetals
1997; American Chemical Society; Volume: 62; Issue: 15 Linguagem: Inglês
10.1021/jo970555l
ISSN1520-6904
AutoresYoshihiro Ushigoe, Yuko Torao, Araki Masuyama, Masatomo Nojima,
Tópico(s)Synthesis and Catalytic Reactions
ResumoOzonolyses 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.
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