Abstract
The synthesis of a series of eight β-naphthyl-substituted 1,2,4-trioxanes 3a– h by a sequence of singlet oxygen ene reaction of allylic alcohols 1a– h and Lewis acid catalyzed peroxyacetalization of the allylic hydroperoxides 2a– h with β-naphthaldehyde is reported. The ene reactions were performed by solid-state photooxygenation in dye-crosslinked polystyrene beads and resulted in mixtures of diastereoisomeric hydroperoxides 2. Boron trifluoride catalyzed peroxyacetalization resulted in the formation of 3, as well as the 1,2,4-trioxanes 4 and 5, which were formed via acid catalyzed β-hydroperoxy alcohol cleavage.
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