65743-07-9Relevant academic research and scientific papers
The Synthesis and Cation-complexing Ability of Alkyl Crown Ethers
Mizuno, Tadashi,Nakatsuji, Yohji,Yanagida, Shozo,Okahara, Mitsuo
, p. 481 - 484 (1980)
Alkyl-15-crown-5 and alkyl-12-crown-4 were prepared via polyethylene glycol β-haloalkyl ethers in two steps from terminal olefins, and their complexing ability with cations of alkali and alkaline earth metals was measured by using 1H NMR; it was found to be almost identified with that of the corresponding unsubstituted crown ether.A new type of alkyl crown ether with a chloro substituent could also be synthesized according to this method.
Enhancement of Cation Binding in Lariat Ethers Bearing a Methyl Group at the Quaternary, Pivot Carbon Atom
Nakatsuji, Yohji,Nakamura, Tetsuya,Okahara, Mitsuo,Dishong, Dennis M.,Gokel, George W.
, p. 1237 - 1242 (2007/10/02)
A number of carbon-pivot lariat ethers have been prepared and compared, with their counterparts having a methyl group bonded to the side-arm-bearing or pivot carbon.All of the compounds examined are 15-crown-5 derivatives, and in this series, the methyl lariats invariably show a higher affinity for sodium than do the nonmethylated species.The results are less consistent in the case of potassium cation which is larger than the 15-crown-5 compound's cation binding hole.The enhanced stability constant observed for sodium with the methyl lariats is attributed to reduced s ide-arm mobility or conformational changes in either the side arm or macroring.
Synthesis of Substituted Crown Ethers from Oligoethylene Glycols
Ikeda, Isao,Yamamura, Shingo,Nakatsuji, Yohji,Okahara, Mitsuo
, p. 5355 - 5358 (2007/10/02)
A convenient synthetic method for preparing 12-crown-4, 15-crown-5, 18-crown-6, and 21-crown-7 bearing various substituents by intramolecular cyclization of the corresponding substituted oligoethylene glycols in high yields is described.Substituents include modifiable pendent groups such as phenyl and hydroxymethyl, as well as various alkyl groups.Stability constants for the new substituted crown ethers with sodium and potassium ions in methanol were determined by potentiometric titration.The absolute effect of pendent groups on stability constants was insignificant.
