Helvetica Chimica Acta p. 943 - 951 (1989)
Update date:2022-09-26
Topics:
Nishio, Takehiko
Mathies, Peter
Job, Kurt
Frei, Bruno
Jeger, Oskar
Photo-oxygenation of (E)-7-methyl-β-ionone ((E)-1) and (E)-8-methyl-β-ionone ((E)-2) gave rise to the formation of the hydroperoxy-enones (E)-10 and (E)-15, respectively, which, in part, underwent intramolecular epoxidation to the hydroxy-epoxy-ketones 11 and 16, respectively.The product distribution of the photo-oxidation of (Z)-1 shows a marked influence of the skewed ground-state conformation of the dienone chromophore.Thus, singlet oxygen (1O2) was added to C(γ) of the dienone chromophore leading to the spirocyclic peroxy-hemiacetal 12 and to the endoperoxide 13.In addition, the tricyclic peroxide 14 was formed as a new type of product via primary addition of 1O2 to C(γ) of the dienone chromophore.The structure of 14 was established by X-ray crystal-structure analysis of the hemiacetal 22.
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