6533b7cffe1ef96bd1257c90
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
Brian M. BarryR. Graeme SoperJuha HurmalainenAkseli MansikkamäkiKatherine N. RobertsonWilliam L. McclennanAlex J. VeinotTracey L. RoemmeleUlrike Werner‐zwanzigerRené T. BoeréHeikki M. TuononenJason A. C. ClyburneJason D. Masudasubject
cumulenes010405 organic chemistryreductionGeneral MedicineN-heterocyclic carbenes010402 general chemistryalkynes01 natural sciencespropargyl cations0104 chemical sciences3. Good healthdescription
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. peerReviewed
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-12-14 |