Spontaneous oxidative cyclisations of 1,3-dihydroxy-4-dimethylallylnaphthalene to tricyclic derivatives?

Organic & Biomolecular Chemistry Pub Date: 2020-03-16 DOI: 10.1039/D0OB00354A

Abstract

The attachment of a dimethylallyl moiety to C4 of 1,3-dihydroxynaphthalene led to spontaneous oxidative cyclisations, resulting in the formation of two tetrahydrobenzofuran and one bicyclo[3.3.1]nonane derivatives. Incubation under an 18O-rich atmosphere proved that both the incorporated oxygen atoms originated from O2. A radical-involved mechanism is proposed for these cyclisations.

Graphical abstract: Spontaneous oxidative cyclisations of 1,3-dihydroxy-4-dimethylallylnaphthalene to tricyclic derivatives
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