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Mono- and Bis-Imidazolidinium Ethynyl Cations and the Reduction of the Latter to give an Extended Bis-1,4-([3]Cumulene)-p-Carbo-Quinoid System.

Angewandte Chemie 2017 November 20
An extended π-system containing two [3]cumulene fragments separated by a p-carbo-quinoid and stabilized by two capping N-heterocyclic carbenes (NHCs) has been prepared. Mono- and bis-imidazolidinium ethynyl cations have also been synthesized from the reaction of an NHC with phenylethynyl bromide or 1,4-bis(bromoethynyl)benzene. Cyclic voltammetry coupled with synthetic and structural studies showed that the dication is readily reduced to a neutral, singlet bis-1,4-([3]cumulene)-p-carbo-quinoid due to the π-accepting properties of the capping NHCs.

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