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- Title
Mono‐ and Bis(imidazolidinium ethynyl) Cations and Reduction of the Latter To Give an Extended Bis‐1,4‐([3]Cumulene)‐<italic>p</italic>‐carboquinoid System.
- Authors
Barry, Brian M.; Soper, R. Graeme; Hurmalainen, Juha; Mansikkamäki, Akseli; Robertson, Katherine N.; McClennan, William L.; Veinot, Alex J.; Roemmele, Tracey L.; Werner‐Zwanziger, Ulrike; Boeré, René T.; Tuononen, Heikki M.; Clyburne, Jason A. C.; Masuda, Jason D.
- Abstract
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.
- Subjects
ETHYNYL compounds; CUMULENES; HETEROCYCLIC compounds; PHENYL compounds; BENZENE; CYCLIC voltammetry
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 3, p757
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201711031