Cyclopalladation of Phenyl-(2,4,6-trimethylbenzylidene)-amine: An Undergraduate Organometallic Laboratory Experiment

Joan Albert , Magali Cadena and Jaume Granell
Departament de Química Inorgànica, Universitat de Barcelona, 08028 Barcelona, Spain
J. Chem. Educ., 2003, 80 (7), p 801
DOI: 10.1021/ed080p801
Publication Date (Web): July 1, 2003

Abstract

The synthesis of a six-membered cyclopalladated complex by activation of a Caliphatic—H bond is reported. The synthesis of this organometallic compound is simple and does not require any special equipment, such as gas cylinders, vacuum lines, or solvents distilled over sodium-benzophenone. This experiment shows that certain organometallic complexes are stable enough to be obtained in acetic acid, under reflux, in the absence of an inert gas atmosphere. Most of the signals that appear in the 1H and 13C NMR spectra of the palladium metallacycle can easily be assigned. In addition, the NMR spectroscopy of organometallic and coordination complexes show that the coupling with other nuclei, such as 31P, should be considered.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

NMR Spectroscopy

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History

  • Received: August 03, 2009

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