Ligandstruktur und Komplexierung, XXXI. Kronenether und Cryptanden mit Urethan‐Struktureinheiten

Buhleier, E.; Frensch, Klaus; Luppertz, Friedhelm; Vögtle, Fritz

doi:10.1002/jlac.197819781005

Cited by 22 publications

(1 citation statement)

References 9 publications

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“…Pyridinophanes have attracted much interest from the structural and functional points of view. Those possessing crown ether moiety were extensively investigated by Vögtle − and Newkome − as host molecules. Other [2.2](2,5)pyridinophanes − and [3.3](2,5)- and (2,6)pyridinophanes 13 were prepared for the structural investigation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Complexing Properties of [2.n](2,6)Pyridinocrownophanes

et al. 2005

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[2.n](2,6)Pyridinocrownophanes (3a-e) were efficiently prepared by intramolecular [2 + 2] photocycloaddition of vinylpyridine derivatives under irradiation using a 400-W high-pressure mercury lamp through a Pyrex filter. They were of cis-configuration with respect to the cyclobutane ring, which was proven by the specific methine proton NMR resonances at delta 3.98-4.08. From ESI-MS analysis 3a-e were found to form 1:1 complexes with Ag+ cation. In a liquid-liquid extraction, 3 showed the highest affinity toward Ag+ cation among several heavy metal nitrates. In this series, 3c possessing four ethereal oxygen atoms was found to show the highest Ag+ affinity, according to the liquid-liquid extraction and determination of stability constant with the cation. The photoreactivity of precursor vinylpyridines is discussed by the predictor gamma(r(c)) proposed by Caldwell.

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