- Synthesis and Complex Formation of Phenyl- and (4-Phenylbutyl)-substituted Crown Ethers
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A number of phenyl and (4-phenylbutyl) derivates of 18-C-6 and 24-C-8 have been prepared: tetraphenyl-diene-18-crown-6 (TPDE-18-C-6), tetraphenyl-18-crown-6 (TP-18-C-6), tetraphenyldiene-24-crown-8 (TPDE-24-C-8), tetraphenyl-24-crown-8 (TP-24-C-8), and bis(4-phenylbutyl)-18-crown-6 (BPB-18-C-6).The ring formation reactions have been carried out by phase-transfer catalysis.All compounds are solids at room temperature except for the liquid BPB-18-C-6 wich represents a mixture of isomers.The syn- and anti-isomers of TP-18-C-6 and TP-24-C-8 have been isolated and identified by x-ray diffraction.The complex formation constants, determined by d. c. polarography in methanol/benzene (80:20 v/v), depend not only on the ring size but also on the number and kind of substituents as well as their steric arrangement.The derivatives of 18-C-6 form the most stable complexes with K+, Sr2+, Ba2+, and Pb2+.The derivatives of 24-C-8 prefer K+, Rb+, and Ba2+.
- Blasius, Ewald,Rausch, Ralf Andreas,Andreetti, Giovanni Dario,Rebizant, Jean
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p. 1113 - 1127
(2007/10/02)
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- UNSATURATED CROWN ETHERS: STILBENO-CROWN ETHERS
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Stilbenocrown ethers 3a,c and 4a,b were synthesized in a cyclization reaction of benzoin with oligoethylene glycol ditosylates (2a-c) under a phase-transfer condition.Extractions of aqueous alkali picrates (Na+-Cs+) were examined with the distilbenocrown ethers 4a,b, the partially-hydrogenated tetraphenylcrown ethers 6a,b, and the fully-hydrogenated tetracyclohexylcrown ethers 7a,b.
- Inoue, Yoshihisa,Ouchi, Mikio,Nakazato, Toshiyo,Matsuda, Takashi,Hakushi, Tadao
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p. 781 - 784
(2007/10/02)
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