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Mono‐ and Bis(imidazolidinium ethynyl) Cations and Reduction of the Latter To Give an Extended Bis‐1,4‐([3]Cumulene)‐p‐carboquinoid System |
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| Authors: | Prof. Brian M. Barry R. Graeme Soper Juha Hurmalainen Akseli Mansikkamäki Dr. Katherine N. Robertson William L. McClennan Alex J. Veinot Dr. Tracey L. Roemmele Dr. Ulrike Werner‐Zwanziger Prof. René T. Boeré Prof. Heikki M. Tuononen Prof. Jason A. C. Clyburne Prof. Jason D. Masuda |
| Affiliation: | 1. Department of Chemistry, Saint Mary's University, Halifax, Nova Scotia, Canada;2. Department of Chemistry, University of Wisconsin-Platteville, Platteville, WI 5, USA;3. Department of Chemistry, Nanoscience Centre, University of Jyv?skyl?, University of Jyv?skyl?, Finland;4. Department of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, Alberta, Canada;5. Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada |
| Abstract: | 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. |
| Keywords: | alkynes cumulenes N-heterocyclic carbenes propargyl cations reduction |