Synthesis of spiroannulated and 3-arylated 1,2,4-trioxanes from mesitylol and methyl 4-hydroxytiglate by photooxygenation and peroxyacetalization

Abstract

Cycloalkanones were utilized in the Lewis acid catalyzed peroxyacetalization of β-hydroperoxy homoallylic alcohols (prepared by the ene reaction of the allylic alcohols mesitylol and methyl 4-hydroxytiglate, respectively, with singlet oxygen) to give spiroannulated 1,2,4-trioxanes 5a-5e and 9a-9e, respectively. A second series of 3-arylated trioxanes 10a-10h, that are available from the hydroperoxy alcohol 4 and benzaldehyde derivatives, was investigated by X-ray crystallography. © 2010 Griesbeck et al; licensee Beilstein-Institut.