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Abstract
The preparation and characterization of products of the chemical and photochemical rearrangements of a 19-membered o,o'-azoxybenzocrown were presented. In photochemical rearrangement, besides expected product i.e. 19-membered o-hydroxy-o,o'-azobenzocrown (19-o-OH), obtained under defined conditions with 75% yield, also other macrocyclic products were isolated and identified, namely: 19-membered p-hydroxy-o,o'-azobenzocrown (19-p-OH), 21-membered o'-hydroxy-o,p'-azobenzocrown (21-o'-OH) and 19-membered macrocycle containing 5-membered ring bearing an aldehyde group (19-al). The structures of two atypical products of the photochemical rearrangement - 21-o'-OH and 19-al - were determined in the solid state by the X-ray method and in solution using NMR spectroscopy. Tautomeric equilibrium of the formed hydroxyazobenzocrowns and its change depending on acidity/basicity of the environment and alkali and alkaline earth metal cations complexation were studied using UV-Vis spectrophotometry, spectrofluorimetry and 1H NMR spectroscopy.
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- Category:
- Articles
- Type:
- artykuły w czasopismach
- Published in:
-
ChemPlusChem
no. 85,
pages 2067 - 2083,
ISSN: 2192-6506 - Language:
- English
- Publication year:
- 2020
- Bibliographic description:
- Wagner-Wysiecka E., Szulc P., Luboch E., Chojnacki J., Szwarc-Karabyka K., Łukasik N., Murawski M., Kosno M.: Photochemical Rearrangement of a 19-Membered Azoxybenzocrown: Products and their Properties// ChemPlusChem -Vol. 85,iss. 9 (2020), s.2067-2083
- DOI:
- Digital Object Identifier (open in new tab) 10.1002/cplu.202000474
- Verified by:
- Gdańsk University of Technology
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