The Journal of organic chemistry · 2005
Synthesis and complexing properties of [2.n](2,6)pyridinocrownophanes.
СтатьяПоддержка исследования: вне правительства СШАНазвание и аннотация: Перевод в очереди
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Inokuma Seiichi, Ide Hayato, Yonekura Tomomi, Funaki Takashi, Kondo Shin-ichi, Shiobara Satoru, Yoshihara Toshitada, Tobita Seiji, Nishimura Jun
Аннотация
[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.