Glucose ferrocenyl-oxazolines: Coordination behavior toward [Pd(?3-allyl)Cl]2 studied by ESI-MS

Author(s): Christian Hartinger, Alexey Nazarov, Mathea Sophia Galanski, Michael Reithofer, Bernhard Keppler
Abstract: Several new oxazolin-2-yl-substituted ferrocenes based on 2-amino-2-deoxy-a-d-glucose were synthesized via the corresponding amides followed by closing the oxazoline-ring with SnCl4. Coordination properties of representatives of the group of mono- and bis-oxazolinyl ferrocenes, 2-ferrocenyl-4,5-(3,4,6-tri-O-acetyl-1,2-dideoxy-d-glucopyrano)-[2, 1-d]-oxazoline and 1,1'-bis{4,5-(3,4,6-tri-O-acetyl-1,2-dideoxy-d- glucopyrano)-[2,1-d]-oxazolin-2-yl}ferrocene, respectively, toward [Pd(?3-allyl)Cl]2 were investigated by electrospray ionization mass spectrometry in positive ion mode and by MS/MS technique. With the monooxazoline derivative mainly a 1:1 complex with the Pd-moiety was found in the mass spectrum while the bisoxazoline yields a stoichiometry of 2:1 (oxazoline:Pd). The latter result is attributed to steric hindrance of the coordination of a second Pd-moiety to the bulky bisoxazolinyl-ferrocene. In the case of 1,1'-bis{4,5-(3,4,6-tri-O-acetyl-1,2-dideoxy-d-glucopyrano)-[2,1- d]-oxazolin-2-yl}ferrocene 9 overlapping of two signals in the m/z range from 955-965 was found which can be assigned to the singly charged adduct [C 36H40FeN2O16 + Pd(?3- C3H5)]+ and a doubly charged Pd-ligand cluster with the general formula Pd2[L(9)]2. In addition, the molecular structure of 1,1'-bis{4,5-(3,4,6-tri-O-acetyl-1,2-dideoxy-d- glucopyrano)-[2,1-d]-oxazolin-2-yl}ferrocene was determined by X-ray diffraction analysis. Œ 2005 Elsevier B.V. All rights reserved.
Organisation(s): Department of Inorganic Chemistry
Journal: Journal of Organometallic Chemistry
Volume: 690
Pages: 3301-3308
No. of pages: 8
ISSN: 0022-328X
Publication date: 2005
Peer reviewed: Yes
Austrian Fields of Science 2012: 1040 Chemistry
Portal url: https://ucrisportal.univie.ac.at/en/publications/3b244a20-6f09-4e0f-8378-a3f7bfacb205