Transformation of 1-alkyl-substituted indene ozonides and the corresponding solvent-derived ozonolysis products to tricyclic peroxides: Isolation and characterization of novel hexoxecane derivative

Peroxycarbenium-Mediated C−C Bond Formation: Applications to the Synthesis of Hydroperoxides and Peroxides

“…The 1,2-dioxolane moiety forms the core of prostaglandins, oxidized lipids, and the plakinic acid family of marine natural products. ,, An otherwise attractive approach to this substructure based upon 1,3-dipolar addition 39-42 is limited by the compatibility of alkenes with ozonolysis, the most common method for the generation of carbonyl oxides . Protonated and metalated carbonyl oxides capable of 1,3-dipolar addition have been generated via acid-catalyzed decomposition of ozonides (1,2,4-trioxolanes). , We were interested in employing Lewis acid-mediated ionization of hydroperoxyacetals to furnish reactive hydroperoxycarbenium ions which would react with alkenes to form 1,2-dioxolanes (Table ). , In particular, we were curious about selective activation of an alkoxide in the presence of a free hydroperoxide and in the relative rate of the desired transformation versus acid-catalyzed disproportionation 8 Synthesis of 1,2-Dioxolanes …”

Recent Advances in the Chemistry of Cyclic Peroxides

“…Acidolysis of ozonides 268 derived from 1-substituted indenes or the corresponding solvent-derived products 269 provides the corresponding symmetrical cyclic dimers 270 which have the hexoxecane ring structure (Scheme 88) [171]. …”