6533b853fe1ef96bd12ad591
RESEARCH PRODUCT
Mono‐ and Bis(imidazolidinium ethynyl) Cations and Reduction of the Latter To Give an Extended Bis‐1,4‐([3]Cumulene)‐ p ‐carboquinoid System
R. Graeme SoperUlrike Werner-zwanzigerRené T. BoeréWilliam L. McclennanKatherine N. RobertsonTracey L. RoemmeleJuha HurmalainenAlex J. VeinotAkseli MansikkamäkiJason D. MasudaHeikki M. TuononenBrian BarryBrian BarryJason A. C. Clyburnesubject
010405 organic chemistryCumuleneGeneral Chemistry010402 general chemistryPhotochemistry01 natural sciencesMedicinal chemistryCatalysis0104 chemical sciences3. Good healthDicationchemistry.chemical_compoundchemistryBromideX-ray crystallographySinglet stateCyclic voltammetryBenzenedescription
An extended π-system containing two [3]cumulene fragments separated by a p-carboquinoid 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-carboquinoid as a result of the π-accepting properties of the capping NHCs.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2018-01-15 | Angewandte Chemie International Edition |