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• W2040391172 endingPage "5957" @default.
• W2040391172 startingPage "5950" @default.
• W2040391172 abstract "The reactions of 3,4-diphenylcyclopent-2-en-1-one, cyclopent-2-en-1-one, 3,4-dimethylcyclopent-2-en-1-one, and 2,3,4,5-tetramethylcyclopent-2-en-1-one with various trialkylsilyl triflates (SiR3 = SiMe3, SiEt3, SiMe2tBu, SiiPr3) result in the formation of the respective cyclopentadienyl silyl ethers in virtually quantitative yields. The reactions of these cyclopentadienes with n-BuLi and FeCl2 give the respective substituted ferrocenyl trialkylsilyl ethers in 48−57% yields, which are synthetic equivalents of hydroxyferrocenes as generated by a suitable cleavage protocol: SiMe3-protected ferrocene alcohols (CH3CN + 10% H2O + Na2CO3); SiEt3 (CH3CN + 10% H2O + Na2CO3 + NaF); and SiMe2tBu protection (NBu4F·3H2O in CH3CN). Carrying out the deprotection in the presence of carbon electrophiles leads to the respective ferrocenyl alkyl ethers in excellent yields. Using 1-chloro-2-tosylethane results in 1,1‘-bis(2-chloroethoxy)-3,3‘,4,4‘-tetraphenylferrocene which was converted into 1,1‘-bis-(2-iodoethoxy)-3,3‘,4,4‘-tetraphenylferrocene in 89% yield, to be finally reacted with diaza-crown ethers (diaza-12-C-4, diaza-15-C-5, diaza-18-C-6). In this manner the respective ferrocene cryptands 23, 24, and 25 were generated as the 1 + 1 products in yields of 67−80%. The coordination of alkali and alkaline earth metal ions within the cavities of these ferrocene cryptands results in large anodic shifts of the redox potentials of the ferrocene units (23, E = +0.290 V; 23 + Ca2+, E = +0.670 V; 23 + Na+, E = +0.505 V; 24, E = +0.285 V; 24 + K+, E = +0.455 V) as determined by cyclic voltammetry. These anodic shifts are correlated with a decrease in the complex stability constant K of the respective metal ion complex (redox-switching effect) and in the case of 23 and Ca2+ amounts to a reduction of K by 3.4 × 106." @default.
• W2040391172 created "2016-06-24" @default.
• W2040391172 creator A5075096274 @default.
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• W2040391172 date "1997-12-01" @default.
• W2040391172 modified "2023-09-24" @default.
• W2040391172 title "Oxaferrocene Cryptands as Efficient Molecular Switches for Alkali and Alkaline Earth Metal Ions" @default.
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• W2040391172 doi "https://doi.org/10.1021/om970681f" @default.
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