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Stable dicationic dioxoliums and fate of their dioxolyl radicals

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Abstract

Stable dicationic dioxolium salts featuring an ancillary vinamidinium pattern were synthesized and characterized. Although highly reactive, they were found otherwise easy to handle under inert atmosphere. This offered the opportunity to generate and study the fate of unknown 1,3-dioxolyl radicals. Depending on substituents, reduction led to the formation of dimers of either dioxolyl or cyclohexadienyl radicals, stemming from a process that is related to the Surzur–Tanner rearrangement. The cyclohexadienyl radical could be characterized in the case of a tri(tert-butyl)phenyl group, which prevents dimerization processes.

Graphical abstract: Stable dicationic dioxoliums and fate of their dioxolyl radicals

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Publication details

The article was received on 25 Feb 2019, accepted on 18 Mar 2019 and first published on 18 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00298G
Citation: Org. Chem. Front., 2019, Advance Article

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    Stable dicationic dioxoliums and fate of their dioxolyl radicals

    M. Devillard, V. Regnier, J. Pecaut and D. Martin, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00298G

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