Ferrocenophanes with two nitrogen atoms in bridging positions via olefin metathesis: synthesis, structure, and solution dynamics

Submitting author affiliation:
Warsaw University of Technology, Faculty of Chemistry, Warsaw, Poland

Beilstein Arch. 2023, 202332. https://doi.org/10.3762/bxiv.2023.32.v1

Published 26 Jul 2023

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This preprint has not been peer-reviewed. When a peer-reviewed version is available, this information will be updated.


The ruthenium-catalysed ring-closing metathesis of 1,1'-ferrocenylmethylamines provided [8]ferrocenophanes with two nitrogen atoms in the bridge and the (E)‑configuration of the newly formed carbon-carbon double bond. The single-crystal diffraction analyses reveal that these compounds are axially chiral, while the distance between the two nitrogen atoms suggests their potential applications as bidentate ligands. The diaza[8]ferrocenophanes display intriguing solution dynamics that was investigated by means of variable temperature NMR spectroscopy. According to theoretical calculations, the most stable conformer of the ferrocenophane in solution has both N‑substituents occupying the pseudoequatorial positions of the macrocycle.

Keywords: ferrocene; Grubbs’ catalyst; olefin metathesis; single crystal X-ray structure; variable temperature NMR

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Rawiak, K.; Mazur, M.; Enkhbold, T.; Sitek, M.; Kulczyk, S.; Paluch, P.; Guńka, P. A.; Koszytkowska-Stawińska, M.; Buchowicz, W. Beilstein Arch. 2023, 202332. doi:10.3762/bxiv.2023.32.v1

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