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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 8, pp 792–794 | Cite as

Photochromic difurylethene bisaldehyde as potential building block for [AA] and [AB]2 macrocyclization

  • Dmytro SysoievEmail author
  • Carolyn Barnes
  • Thomas Huhn
Article

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.

Keywords

difurylethene bisaldehyde Schiff base macrocycle McMurry reaction 

Notes

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.

Supplementary material

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ESM 1 (PDF 1377 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.University of KonstanzKonstanzGermany
  2. 2.Institute of Organic Chemistry and BiochemistryPragueCzech Republic

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