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
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Date
2017
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.
Journal Title
Journal ISSN
Volume Title
Publisher
Wiley
Abstract
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 1,4bis(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 πaccepting properties of the capping NHCs
Description
Sherpa Romeo yellow journal. This is the peer reviewed version. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions
Keywords
Alkynes , Cumulenes , N-heterocycliccarbenes , Propargylcations , Reduction
Citation
Barry, B. M., Soper, R. G., Hurmalainen, J., Mansikkamäki, A., Robertson, K. N., McClennan, W. L.,...Masuda, J. D. (2017). Angewandte Chemie International Edition, 57(3), 749-754. DOI:10.1002/anie.201711031