Mono‐ and Bis(imidazolidinium ethynyl) Cations and Reduction of the Latter To Give an Extended Bis‐1,4‐([3]Cumulene)‐p-carboquinoid System
Barry, B. M., Soper, R. G., Hurmalainen, J., Mansikkamäki, A., Robertson, K. N., McClennan, W., Veinot, A. J., Roemmele, T. L., Werner‐Zwanziger, U., Boeré, R. T., Tuononen, H. M., Clyburne, J. A. C., & Masuda, J. D. (2018). Mono‐ and Bis(imidazolidinium ethynyl) Cations and Reduction of the Latter To Give an Extended Bis‐1,4‐([3]Cumulene)‐p-carboquinoid System. Angewandte Chemie, 57(3), 749-754. https://doi.org/10.1002/anie.201711031
Julkaistu sarjassa
Angewandte ChemieTekijät
Päivämäärä
2018Oppiaine
Epäorgaaninen kemiaEpäorgaaninen ja analyyttinen kemiaNanoscience CenterInorganic ChemistryInorganic and Analytical ChemistryNanoscience CenterTekijänoikeudet
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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.
Julkaisija
WileyISSN Hae Julkaisufoorumista
1433-7851Julkaisu tutkimustietojärjestelmässä
https://converis.jyu.fi/converis/portal/detail/Publication/117812313
Metadata
Näytä kaikki kuvailutiedotKokoelmat
Rahoittaja(t)
Emil Aaltosen Säätiö srLisätietoja rahoituksesta
J.D.M., J.A.C.C., and R.T.B. acknowledge the support of individual Discovery Grants from the Natural Sciences and Engineering Research Council as well as individual funding from the Canadian Foundation for Innovation, the Nova Scotia Research and Innovation Trust (J.D.M., J.A.C.C.), and the Government of Alberta (R.T.B.). J.A.C.C. is thankful to the Government of Canada for a Canada Research Chair. H.M.T., A.M., and J.H. acknowledge financial support from the University of Jyväskylä and the Emil Aaltonen Foundation as well as computational resources provided by CSC—IT Centre for Science and the Finnish Grid and Cloud Infrastructure (persistent identifier urn:nbn:fi:research infras2016072533). U.W.-Z. acknowledges support from the NMR-3 facility at Dalhousie University. Michel B. Johnson is acknowledged for collecting the magnetic susceptibility data. ...Lisenssi
Samankaltainen aineisto
Näytetään aineistoja, joilla on samankaltainen nimeke tai asiasanat.
-
Extending the Series: Synthesis and Characterization of a Dicationic N-Heterocyclic Selenium Carbene Analogue
Dutton, Jason; Tuononen, Heikki; Jennings, Michael; Ragogna, Paul (ACS, 2006)The room-temperature reaction between the Dipp2DAB ligand, SnCl2, and SeCl4 results in the quantitative formation of a dicationic N-heterocyclic “carbenoid”. This represents the first example of a chalcogenium dication ... -
Preparation and Characterization of P2BCh Ring Systems (Ch=S, Se) and Their Reactivity with N-Heterocyclic Carbenes
Graham, Cameron M. E.; Millet, Clément R. P.; Price, Amy N.; Valjus, Juuso; Cowley, Michael J.; Tuononen, Heikki; Ragogna, Paul J. (Wiley-VCH., 2018)Four-membered rings with a P2BCh core (Ch = S, Se) have been synthesized via reaction of phosphinidene chalcogenide (Ar*P=Ch) and phosphaborene (Mes*P=BNR2). The mechanistic pathways towards these rings are explained ... -
N-Heterocyclic Carbene Catalyzed Quadruple Domino Reactions through α,β-Unsaturated Acyl Azolium Intermediates : Asymmetric Synthesis of Cyclopenta[c]chromenones
Liu, Qiang; Chen, Xiang-Yu; Puttreddy, Rakesh; Rissanen, Kari; Enders, Dieter (Wiley, VCH Verlag GmbH & Co. KGaA, 2018)An N‐heterocyclic carbene catalyzed domino sequence via α,β‐unsaturated acyl azolium intermediates has been developed. This strategy provides a convenient enantioselective route to functionalized tricyclic coumarin derivatives ... -
Isolation of Free Phenylide-like Carbanions with N-Heterocyclic Carbene Frameworks
Krahulic, Kelly; Tuononen, Heikki; Parvez, Masood; Roesler, Roland (ACS, 2009)A series of 1,3-bis(2,6-diisopropylphenyl)-5-methyl-1,3-diaza-4,6-diborabenzenes with methyl, phenyl, and dimethylamino substituents on the ring boron atoms were prepared using the cyclocondensation reaction between ... -
Ammonia Activation by a Nickel NCN-Pincer Complex featuring a Non-Innocent N-Heterocyclic Carbene: Ammine and Amido Complexes in Equilibrium
Brown, Rudy M.; Garcia, Javier Borau; Valjus, Juuso; Roberts, Christopher; Tuononen, Heikki; Parvez, Masood; Roesler, Roland (Wiley - VCH Verlag GmbH & Co. KGaA, 2015)A Ni0-NCN pincer complex featuring a six-membered N-heterocyclic carbene (NHC) central platform and amidine pendant arms was synthesized by deprotonation of its NiII precursor. It retained chloride in the square-planar ...
Ellei toisin mainittu, julkisesti saatavilla olevia JYX-metatietoja (poislukien tiivistelmät) saa vapaasti uudelleenkäyttää CC0-lisenssillä.