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Issue 13, 2018
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The serendipitous discovery of a readily available redox-bistable molecule derived from cyclic(alkyl)(amino)carbenes

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Abstract

Bis(azoliums) are readily available in one step from cyclic (alkyl)(amino)carbenes and bis(acyl chlorides). A two-electron reduction of the bis(azolium), featuring a gem-(dimethyl)malonoyl spacer, leads to the corresponding transient diradical, which undergoes an intramolecular cyclization. The latter can be re-oxidized at a higher potential to yield back the bis(azolium). The redox bistability of this simple organic molecular system is linked to the formation of a weak C–O bond (27 kcal mol−1). Both redox forms can be isolated and stored for months without evidence of decay.

Graphical abstract: The serendipitous discovery of a readily available redox-bistable molecule derived from cyclic(alkyl)(amino)carbenes

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Publication details

The article was received on 02 May 2018, accepted on 18 May 2018 and first published on 21 May 2018


Article type: Research Article
DOI: 10.1039/C8QO00447A
Citation: Org. Chem. Front., 2018,5, 2073-2078
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    The serendipitous discovery of a readily available redox-bistable molecule derived from cyclic(alkyl)(amino)carbenes

    J. K. Mahoney, V. Regnier, E. A. Romero, F. Molton, G. Royal, R. Jazzar, D. Martin and G. Bertrand, Org. Chem. Front., 2018, 5, 2073
    DOI: 10.1039/C8QO00447A

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