59970-10-4Relevant articles and documents
Cation Transport Using Antraquinone-Derived Lariat Ethers and Podands: The First Example of Electrochemically Switched ''On/Off'' Activation/Deactivation
Echegoyen, Lourdes E.,Yoo, Hyunsook Kim,Gatto, Vincent J.,Gokel, George W.,Echegoyen, Luis
, p. 2440 - 2443 (1989)
Antraquinone undergoes one- and two-electron reduction to form either radical anions or dianions.When a crown-ather-type macrocycle or a polyethyleneoxy side chain is attached, the reduced aromatic and the oxygen donor groups cooperate to bind the cation.Binding of Li(1+) or Na(1+) is greater when antraquinone is reduced because there is a charge-charge intraction between it and the cation.This property has been used to facilitate transport.Thus, reduction at the source phase enhances cation binding, and oxidation in the receiving phase induces cation release.Activation/deactivation was effected electrochemically.The ligands studied in a bulk CH2Cl2 phase were 1-((9,10-dioxo-1-oxanthracenyl)methyl)-15-crown-5, 1; 1-((9,10-dioxo-1-oxanthracenyl)methyl)-18-crown-6, 2; 1-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)anthracene-9,10-dione, 3; 1-(2-(2-(2-(2-octadecyloxyethoxy)ethoxy)ethoxy)ethoxy)anthracene-9,10-dione, 4.The first example of an electrochemically activated (reduction) and deactivated (oxidation) cation transport system based on anthraquinone ligands is demonstrated.
Combinatorial synthesis of PEG oligomer libraries
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Page/Page column 9, (2010/02/15)
A simple chain-extending approach was established for the scale-up of the monoprotected monodisperse PEG diol materials. Reactions of THP-(OCH2CH2)n—OMs (n=4, 8, 12) with a large excess of commercially available H—(OCH2CH2)n—OH (n=1-4) under basic conditions led to THP-(OCH2CH2)n—OH (n=5-15). Similarly, Me-(OCH2CH2)n—OH (n=4-11, 13) were prepared from Me-(OCH2CH2)n—OMs (n=3, 7, 11). For the chain elongation steps, 40-80% yields were achieved through extraction purification. PEG oligomer libraries I and II were generated in 50-95% overall yields by alkylation or acylation of THP-(OCH2CH2)n—OH (n=1-15) followed by deprotection. Alkylation of Me-(OCH2CH2)n—OH (n=1-11, 13) with X—(CH2)m—CO2R (X=Br or OMs) and subsequent hydrolysis led to PEG oligomer library III in 30-60% overall yields. Combinatorial purification techniques were adapted to the larger-scale library synthesis. A total of 498 compounds, each with a weight of 2-5 g and a minimum purity of 90%, were synthesized.
HETEROANALOGUES OF 1-TRIACONTANOL
Kocian, Oldrich,Stransky, Karel,Zavada, Jiri
, p. 1356 - 1366 (2007/10/02)
A synthesis of twelve heteroanalogues II-XIII of the plant growth stimulator 1-triacontanol (I), derived from the parent alcohol by a replacement of 1-4 methylene units by heteroatoms O,S,NH and/or by a replacement of 1-2 ethylene units by -CO-O-, -CO-NH- or groups is reported.Spectral and gas-chromatographic properties (Kovats retention indices) of the compounds are described.