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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dc.contributor.authorBarry, Brian M.
dc.contributor.authorSoper, R. Graeme
dc.contributor.authorHurmalainen, Juha
dc.contributor.authorMansikkamäki, Akseli
dc.contributor.authorRobertson, Katherine N.
dc.contributor.authorMcClennan, William L.
dc.contributor.authorVeinot, Alex J.
dc.contributor.authorRoemmele, Tracey L.
dc.contributor.authorWerner-Zwanziger, Ulrike
dc.contributor.authorBoeré, René T.
dc.contributor.authorTuononen, Heikki M.
dc.contributor.authorClyburne, Jason A. C.
dc.contributor.authorMasuda, Jason D.
dc.date.accessioned2019-04-25T19:16:11Z
dc.date.available2019-04-25T19:16:11Z
dc.date.issued2017
dc.descriptionSherpa 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 Versionsen_US
dc.description.abstractAn 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 NHCsen_US
dc.description.peer-reviewYesen_US
dc.identifier.citationBarry, 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.201711031en_US
dc.identifier.urihttps://hdl.handle.net/10133/5343
dc.language.isoen_USen_US
dc.publisherWileyen_US
dc.publisher.departmentDepartment of Chemistry and Biochemistryen_US
dc.publisher.facultyArts and Scienceen_US
dc.publisher.institutionSaint Mary's Universityen_US
dc.publisher.institutionUniversity of Wisconsin-Plattevilleen_US
dc.publisher.institutionUniversity of Jyvaskylaen_US
dc.publisher.institutionUniversity of Lethbridgeen_US
dc.publisher.institutionDalhousie Universityen_US
dc.publisher.urlhttps://doi.org/10.1002/anie.201711031
dc.subjectAlkynesen_US
dc.subjectCumulenesen_US
dc.subjectN-heterocycliccarbenesen_US
dc.subjectPropargylcationsen_US
dc.subjectReductionen_US
dc.titleMono- and bis-imidazolidinium ethynyl cations and the reduction of the latter to give an extended bis-1,4-([3]cumulene)-p-carbo-quinoid systemen_US
dc.typeArticleen_US
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