Catalyst- and template-free condensation of photochromic difurylethene bisaldehyde with o-phenylenediamine led to selective formation of macrocyclic Schiff base [AB]2 product. Application of the same difurylethene bisaldehyde in the McMurry reaction resulted in cyclic dimer formation in moderate yield. No linear oligomers were observed in both approaches.
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Financial support from the DFG (grant No. HU 1682/3-1) is gratefully acknowledged. Authors thank Dr. G. Auffermann for carrying out the elemental analysis at the Analytical Facility of Max Planck Institute for Chemical Physics of Solids (Dresden) and U. Haunz (University of Konstanz) for recording a solid-state 13C NMR spectrum.
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Supplementary information file containing 1H, 13C, 19F NMR spectra, 1H–13C HSQC and 1H–13C HMBC spectra, and mass spectra of the synthesized compounds is available from the journal website http://link.springer.com/journal/10593.
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(8), 792–794
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Sysoiev, D., Barnes, C. & Huhn, T. Photochromic difurylethene bisaldehyde as potential building block for [AA] and [AB]2 macrocyclization. Chem Heterocycl Comp 55, 792–794 (2019). https://doi.org/10.1007/s10593-019-02538-x
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DOI: https://doi.org/10.1007/s10593-019-02538-x