Host-guest complexation. 9. Macrocyclic polyethers and sulfides shaped by one rigid dinaphthyl unit and attached arms. Synthesis and survey of complexing abilities was written by Cram, Donald J.;Helgeson, Roger C.;Koga, Kenji;Kyba, Evan P.;Madan, Khorshed;Sousa, Lynn R.;Siegel, Merrell G.;Moreau, Patrice;Gokel, George W.. And the article was included in Journal of Organic Chemistry in 1978.Electric Literature of C11H16O3 This article mentions the following:
The synthesis and characterization of a stereoisomeric macrocyclic polyether, e.g., I (R, R2 = H, CH2OH, CH2OCH2CO2Me, etc.; R1 = H, Br, COMe, etc.) and polyether-polythioether hosts are described. The unshared electron pairs of the heteroatoms act as binding sites for metal or alkylammonium cations. Substituents attached at the 3,3′-positions of the 1,1′-binaphthyl unit converge on and provide addnl. shape to the space surrounding the central binding hole of the macro ring. Certain of these units terminate in functional groups that provide addnl. ligands for cationic guests, in some cases supplying counterions for the charge on the guests. Substituents attached at the 6,6′-positions of the 1,1′-binaphthyl unit diverge from the macro ring and its environment and can be used to manipulate solubility properties or to bind the hosts to solid supports. Substituents attached at the 3- or 4-positions of the 1,2-benzene units, when long enough and in the proper conformations, can curl to place addnl. binding sites on the edge of the macro ring. The maximum rotations and absolute configurations of some of the optically active hosts were determined Ring closures (6-65% yield) involved aryloxide- or arylsulfide-anion substitutions on appropriate alkyl ditosylates. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Electric Literature of C11H16O3).
3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Electric Literature of C11H16O3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem