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Regioselective C-C bond formation between ethylene and α-naphthylcarbaldimines catalyzed by Ru₃(Co)₁₂: NMR spectroscopic investigations on the proceeding of the reaction

Journal of Molecular Catalysis A : Chemical. Bd. 165. H. 1-2. Amsterdam: Elsevier 2001 S. 37 - 43

Erscheinungsjahr: 2001

ISBN/ISSN: 1381-1169

Publikationstyp: Zeitschriftenaufsatz

Sprache: Englisch

Doi/URN: 10.1016/S1381-1169(00)00424-6

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Inhaltszusammenfassung


The reaction of ethylene with imines derived from alpha -naphthylcarbaldehyde catalyzed by Ru-3(CO)(12) leads to the selective and quantitative formation of products in which one molecule of ethylene has been inserted into the C-H bond in ortho position with respect to the exocyclic imine substituent. The stoichiometric reaction of the same ligands with Ru-3(CO)(12) leads to dinuclear ruthenium carbonyl complexes showing the same regioselectivity of C-H activation but the hydrogen atom is shi...The reaction of ethylene with imines derived from alpha -naphthylcarbaldehyde catalyzed by Ru-3(CO)(12) leads to the selective and quantitative formation of products in which one molecule of ethylene has been inserted into the C-H bond in ortho position with respect to the exocyclic imine substituent. The stoichiometric reaction of the same ligands with Ru-3(CO)(12) leads to dinuclear ruthenium carbonyl complexes showing the same regioselectivity of C-H activation but the hydrogen atom is shifted in an intramolecular hydrogen transfer reaction towards the former imine carbon atom. If the catalytic alkylation of alpha -naphthylcarbaldimines is monitored by NMR the occurrence of the dinuclear product of the stoichiometric reaction is observed before the reaction again quantitatively yields the imines bearing an ethyl group in 2-position of the naphthalene core. This proofs that there must be an equilibrium between the dinuclear ruthenium carbonyl complex which is also observed if alpha -naphthylcarbaldimines are treated with an equimolar amount of Ru-3(CO)(12) and another ruthenium compound where the ethylene might be inserted catalytically into a ruthenium carbon bond. (C) 2001 Elsevier Science B.V. All rights reserved. » weiterlesen» einklappen

  • Alkylation
  • C-C bond formation
  • C-H activation
  • Olefin insertion
  • Ruthenium

Autoren


Berger, Daniel (Autor)
Göbel, Angela (Autor)

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Beteiligte Einrichtungen