Proton-ionizable crown compounds. 16. Synthesis, structural features, and cation transport studies of crown ethers containing the 4-pyridone n-hydroxide subcyclic group
Pyridino-14-crown-4, two 4-(2-tetrahydropyranoxy)pyridino-14-crown-4 compounds, and the corresponding 4-(2-tetrahydropyranoxy)pyridino-15-crown-5 and -18-crown-6 compounds were oxidized to the N-oxide analogues by treatment with m-chloroperbenzoic acid. Upon hydrolysis, the tetrahydropyranoxy-substituted compounds became the N-hydroxy-4-pyridono-crown compounds in solution. A crystal structure determination of one of the new crowns showed that the 4-hydroxypyridine N-oxide was the stable form in the solid state. Of the alkali-metal cations, the n-octyl-substituted 1-hydroxy-4-pyridono-14-crown-4 compound transported lithium ions selectively in an aqueous metal hydroxide-methylene chloride-0.01 M aqueous hydrochloric acid bulk liquid membrane system. 28 references, 3 figures, 7 tables.
- Research Organization:
- Brigham Young Univ., Provo, UT (USA)
- DOE Contract Number:
- FG02-86ER13463
- OSTI ID:
- 6083861
- Journal Information:
- J. Org. Chem.; (United States), Vol. 53:12
- Country of Publication:
- United States
- Language:
- English
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ORGANIC NITROGEN COMPOUNDS
SYNTHESIS
POLYETHYLENE GLYCOLS
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EXPERIMENTAL DATA
LITHIUM COMPOUNDS
ALCOHOLS
ALKALI METAL COMPOUNDS
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400201* - Chemical & Physicochemical Properties