Spontaneous oxidative cyclisations of 1, 3-dihydroxy-4-dimethylallylnaphthalene to tricyclic derivatives. Issue 14 (24th March 2020)

• Record Type: Journal Article
• Authors: Wang, Jinglin; Ran, Huomiao; Xie, Xiulan; Wang, Kaiping; Li, Shu-Ming
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 14(2020)
• Page Start: 2646
• Page End: 2649
• Publication Date: 2020-03-24
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob00354a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Radical-involved spontaneous oxidative cyclisations of 1, 3-dihydroxy-4-dimethylallylnaphthalene are reported. 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 18 O-rich atmosphere proved that both the incorporated oxygen atoms originated from O2 . A radical-involved mechanism is proposed for these cyclisations.