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Issue 14, 2020
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Spontaneous oxidative cyclisations of 1,3-dihydroxy-4-dimethylallylnaphthalene to tricyclic derivatives

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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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Article information


Submitted
17 Feb 2020
Accepted
16 Mar 2020
First published
16 Mar 2020

Org. Biomol. Chem., 2020,18, 2646-2649
Article type
Communication

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

J. Wang, H. Ran, X. Xie, K. Wang and S. Li, Org. Biomol. Chem., 2020, 18, 2646
DOI: 10.1039/D0OB00354A

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