6-hydroxymethyl-1,2,4-trioxanes and derivatives: An alternative 1,2,4-trioxane synthesis from β′γ′-unsaturated β-hydroxyhydroperoxides

Article abstract of DOI:10.1016/0040-4039(94)80048-0

Allylic hydroperoxides CH₂:C(Ph)CH(OOH)CH₂OX (X = H, CONHPh, Ac), from regiospecific photooxygenation of allylic alcohols CH₃C(Ph):CHCH₂OX, form hemiperoxyacetals with aldehydes or ketones which upon cyclisation with mercury(II) trifluoroacetate then reduction with sodium borohydride diastereoselectively afford 1,2,4-trioxanes with XOCH₂ substituents at C-6.