Synthesis and Chemistry of Perfluoro Macrocycles

The perfluoro macrocycles perfluoro-18-crown-6, perfluoro-12-crown-4, perfluoro-15-crown-5, perfluoro-cyclohexano-15-crown-5, perfluorodicyclohexano-18-crown-6, perfluorodicyclohexano-24-crown-8, and perfluoro-4,7,13,16,21,24-hexaoxa-1, 10-diazabicyclo[8,8,8] hexacosane(perfluorocryptand [222]) have...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1994-06, Vol.116 (12), p.5172-5179
Main Authors: Lin, Tzuhn-Yuan, Lin, Wen-Huey, Clark, Wayne D, Lagow, Richard J, Larson, Steven B, Simonsen, Stanley H, Lynch, Vincent M, Brodbelt, Jennifer S, Maleknia, Simin D, Liou, Chien-Chung
Format: Article
Language:English
Subjects:
400102 - Chemical & Spectral Procedures
400201 - Chemical & Physicochemical Properties
CHEMICAL REACTIONS
CHROMATOGRAPHY
COHERENT SCATTERING
COMPILED DATA
CROWN ETHERS
CRYSTAL STRUCTURE
DATA
DIFFRACTION
ETHERS
FLUORINATION
GAS CHROMATOGRAPHY
HALOGENATION
INFORMATION
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
MASS SPECTROSCOPY
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
SCATTERING
SEPARATION PROCESSES
SPECTROSCOPY
SYNTHESIS
X-RAY DIFFRACTION
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Description
Summary:The perfluoro macrocycles perfluoro-18-crown-6, perfluoro-12-crown-4, perfluoro-15-crown-5, perfluoro-cyclohexano-15-crown-5, perfluorodicyclohexano-18-crown-6, perfluorodicyclohexano-24-crown-8, and perfluoro-4,7,13,16,21,24-hexaoxa-1, 10-diazabicyclo[8,8,8] hexacosane(perfluorocryptand [222]) have been prepared by carefully controlled elemental fluorination. Although they are much weaker bases than their hydrocarbon analogues, these perfluoromacrocycles are very stable materials which should have a number of applications. The crystal structures of perfluoro-18-crown-6 and of a perfluorodicyclohexano-18-crown-6 isomer are reported. Gas-phase studies with several perfluoro crown ethers and with the perfluorocryptand [222] have shown that such macrocycles tenaciously bind O[sub 2][sup [minus]] and F[sup [minus]]. Perfluoro crown ethers and cryptands coordinate anions preferentially over cations. The collisionally activated mass spectra of several perfluoro macrocylic ions are described. 38 refs., 8 figs., 4 tabs.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00091a022